US 6,297,373 B1Granted

Method for acylating hexakis (arylmethyl) hexaazaisowurtzitane

AssigneeAsahi Kasei Kabushiki Kaisha

InventorsTamotsu Kodama, Naoko Ishihara, Haruyuki Minoura, Nobuhisa Miyake, Setsuo Yamamatsu

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Abstract

A method for acylating a hexakis (arylmethyl) hexaazaisowurtzitane (WB6) by reductively removing the arylmethyl groups in the presence of an acylating agent, characterized by contacting a WB6 (a) with a heterogeneous system reduction catalyst (b) in the presence of an acylating agent (c) and a reducing agent (d) in a solvent (e) for the WB6 (a) to reductively remove the arylmethyl groups from the WB6 (a) and acylate the same, and by preventing the WB6 (a) and the catalyst (b) from being contacted with each other when at least either of the acylating agent (c) and the reducing agent (d) is not present. In this method, the decomposition of the WB6 skeleton, which readily occurs in the beginning of the acylation of the WB6 as a starting material, can be highly effectively inhibited. This method can hence stably produce a tetraacylhexaazaisowurtzitane derivative in a high yield and is industrially advantageous.

Claims4

Dependent claims

A method for acylating a hexakis(arylmethyl)hexaazaisowurtzitane by reductive dearylmethylation in the presence of an acylating agent, said hexakis(arylmethyl)hexaazaisowurtzitane being represented by the following formula (1):

WB6 (1)
wherein each B independently represents a C7-C21 arylmethyl group, and W represents a hexavalent hexaazaisowurtzitane residue represented by the following formula (2):
which comprises contacting (a) a hexakis(arylmethyl)hexaazaisowurtzitane and (b) a heterogeneous reduction catalyst with each other in the presence of (c) an acylating agent and (d) hydrogen gas in (e) an amide group-containing solvent for said hexakis(arylmethyl)hexaazaisowurtzitane (a), thereby performing a reductive dearylmethylation/acylation reaction of said hexakis(arylmethyl)hexaazaisowurtzitane (a) to obtain a reaction mixture containing at least one tetraacylhexaazaisowurtzitane compound represented by the following formula (3):
WA4BnH(2−n) (3)
wherein n is an integer of 0 to 2, each A independently represents a C1-C10 acyl group, H represents a hydrogen atom, and each of B and W is as defined above,
wherein there is no contact between said hexakis(arylmethyl)hexaazaisowurtzitane (a) and said heterogeneous reduction catalyst (b) in the absence of any of said acylating agent (c) and said hydrogen gas (d).

3 more elements

Dependencies are inferred from the claim text.