US 2004/0002547 A1 · Preparations of a sulfinyl acetamide

Abstract

The present invention provides processes for the preparation of modafinil which includes the step of reacting benzhydrylthiol and chloroacetamide.

Dependent claims

A process of preparing modafinil comprising the step of reacting chloroacetamide with benzhydrylthiol to form 2-(benzhydrylthiyl) acetarmide.

A process of preparing modafinil comprising:

(1) reacting benzhydrol, thiourea (about 1-3 equivalents) and an aqueous 48% HBr solution (about 1-3 equivalents) in aqueous tetrahydrofuran at about 70° C. to form S-benzhydrylthiouronium salt;
(2) reacting the S-benzhydrylthiouronium salt with an aqueous potassium hydroxide solution (about 2-5 equivalents) at about 70° C. to form benzhydrylthiol;
(3) reacting chloroacetamide (about 1.05-2 equivalents) in an aqueous tetrahydrofuran solution, with the benzhydrylthiol at about 70° C., to form 2-(benzhydrylthiyl) acetamide;
(4) reacting the 2-(benzhydrylthiyl) acetamide with acetic acid (about 2-5 equivalents) and a 30% aqueous hydrogen peroxide solution (about 1.2-2 equivalents) to form modafinil.

1 more element

A process of preparing modafinil comprising:

(1) reacting benzhydrol, thiourea (about 1-3 equivalents) and an aqueous 48% HBr solution (about 1-3 equivalents) in aqueous chlorobenzene at about 70° C. to form S-benzhydrylthiouronium salt;
(2) reacting the S-benzhydrylthiouronium salt with an aqueous potassium hydroxide solution (about 2-5 equivalents) at about 70° C. to form benzhydrylthiol;
(3) reacting chloroacetamide (about 1.05-2 equivalents) in powder form with the benzhydrylthiol at about 70° C., to form 2-(benzhydrylthiyl) acetamide;
(4) reacting the 2-(benzhydrylthiyl) acetamide with acetic acid (about 2-5 equivalents) and a 30% aqueous hydrogen peroxide solution (about 1.2-2 equivalents) to form modafinil.

1 more element

Dependencies are inferred from the claim text.

The present invention provides processes for the preparation of modafinil which includes the step of reacting benzhydrylthiol and chloroacetamide.

Dependent claims

A process of preparing modafinil comprising the step of reacting chloroacetamide with benzhydrylthiol to form 2-(benzhydrylthiyl) acetarmide.

A process of preparing modafinil comprising:

(1) reacting benzhydrol, thiourea (about 1-3 equivalents) and an aqueous 48% HBr solution (about 1-3 equivalents) in aqueous tetrahydrofuran at about 70° C. to form S-benzhydrylthiouronium salt;
(2) reacting the S-benzhydrylthiouronium salt with an aqueous potassium hydroxide solution (about 2-5 equivalents) at about 70° C. to form benzhydrylthiol;
(3) reacting chloroacetamide (about 1.05-2 equivalents) in an aqueous tetrahydrofuran solution, with the benzhydrylthiol at about 70° C., to form 2-(benzhydrylthiyl) acetamide;
(4) reacting the 2-(benzhydrylthiyl) acetamide with acetic acid (about 2-5 equivalents) and a 30% aqueous hydrogen peroxide solution (about 1.2-2 equivalents) to form modafinil.

1 more element

A process of preparing modafinil comprising:

(1) reacting benzhydrol, thiourea (about 1-3 equivalents) and an aqueous 48% HBr solution (about 1-3 equivalents) in aqueous chlorobenzene at about 70° C. to form S-benzhydrylthiouronium salt;
(2) reacting the S-benzhydrylthiouronium salt with an aqueous potassium hydroxide solution (about 2-5 equivalents) at about 70° C. to form benzhydrylthiol;
(3) reacting chloroacetamide (about 1.05-2 equivalents) in powder form with the benzhydrylthiol at about 70° C., to form 2-(benzhydrylthiyl) acetamide;
(4) reacting the 2-(benzhydrylthiyl) acetamide with acetic acid (about 2-5 equivalents) and a 30% aqueous hydrogen peroxide solution (about 1.2-2 equivalents) to form modafinil.

1 more element

Dependencies are inferred from the claim text.