# US 5,326,899 A · Process for preparation of iodopropargyl carbamates

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- Number: US 5,326,899 A
- Document ID: US5326899A
- Status: Granted
- Kind: A
- Application number: 08/076,561
- Filed: 1993-06-14
- Granted: 1994-07-05
- Earliest claimed: 1993-06-14
- Assignees: Rohm and Haas Company
- Inventors: Barry C. Lange
- Web page: https://patentgrep.com/patent/US5326899A

## CPC

- C07C 269/04: from amines with formation of carbamate groups
- C07C 271/12: to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A Process for producing N-alkyl iodopropargyl carbamate comprising: A. reacting a dialkyl(C.sub.1 -C.sub.3) carbonate with propargyl alcohol in the presence of a first catalyst under conditions to produce dipropargyl carbonate; B. reacting said dipropargyl carbonate with an alkyl(C.sub.1 -C.sub.6)amine, optionally in the presence of a second catalyst, to produce N-alkyl(C.sub.1 -C.sub.6) propargyl carbamate; C. reacting said N-alkyl(C.sub.1 -C.sub.6) propargyl carbamate with an iodinating agent to produce N-alkyl(C.sub.1 -C.sub.6) iodopropargyl carbamate is disclosed.

## Claims

### Claim 1

Process for producing N-alkyl iodopropargyl carbamate comprising:
A. reacting a dialkyl(C.sub.1 -C.sub.3) carbonate with propargyl alcohol in the presence of a first catalyst under conditions to produce dipropargyl carbonate;
B. reacting said dipropargyl carbonate with an alkyl(C.sub.1 -C.sub.6)amine to produce N-alkyl(C.sub.1 -C.sub.6) propargyl carbamate;
C. reacting said N-alkyl(C.sub.1 -C.sub.6) propargyl carbamate with an iodinating agent to produce N-alkyl(C.sub.1 -C.sub.6) iodopropargyl carbamate.

### Claim 2 (depends on 1)

Process according to claim 1 wherein said dialkyl carbonate is selected from the group consisting of dimethyl carbonate and diethyl carbonate.

### Claim 3 (depends on 1)

Process according to claim 1 wherein said alkyl(C.sub.1 -C.sub.6)amine is butylamine.

### Claim 4 (depends on 1)

Process according to claim 1 wherein said first catalyst is selected from the group consisting of boron tribomide, trimethylsilyliodide/iodine, potassium cyanide, Al.sub.2 O.sub.3, ammonia, n-butyl lithium, alkali metal alkoxide, potassium-butoxide/molecular sieves, dimethylaminopyridine, Ti(OCH.sub.2 CH.sub.3).sub.4 and p-toluenesulfonic acid.

### Claim 5 (depends on 1)

Process according to claim 1 wherein said first catalyst is alkali metal alkoxide.

### Claim 6 (depends on 5)

Process according to claim 5 wherein said alkali metal alkoxide is selected from the group consisting of sodium methoxide, potassium methoxide, sodium ethoxide and potassium ethoxide.

### Claim 7 (depends on 1)

Process according to claim 1 wherein said dipropargyl carbonate is reacted with said alkyl(C.sub.1 -C.sub.6)amine to produce said N-alkyl(C.sub.1 -C.sub.6) propargyl carbamate in the presence of a second catalyst.

### Claim 8 (depends on 7)

Process according to claim 7 wherein said second catalyst is acetic acid.

### Claim 9 (depends on 1)

Process according to claim 1 wherein said dialkyl carbonate is dimethyl carbonate, said alkyl(C.sub.1 -C.sub.6)amine is butylamine, said first catalyst is sodium methoxide, said second catalyst is acetic acid, and said iodinating agent is a mixture of iodine and sodium hydroxide.

### Claim 10 (depends on 1)

Process according to claim 1 wherein said iodinating agent is a mixture of iodine and a base.