Phosgene → 2-Phenoxycarbonylhydrazinecarbonyl chloride

HRID 615909Notes

Reaction equation

HRID 615909 reaction equation
[C:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:4])[NH:2][NH2:3].C(OCC)(=O)NN.[C:19](Cl)([Cl:21])=[O:20]>ClCCl>[O:5]([C:1]([NH:2][NH:3][C:19]([Cl:21])=[O:20])=[O:4])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 134791Hydrazinecarboxylic acid, phenyl ester

Product 1

HCID 204068552-Phenoxycarbonylhydrazinecarbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Example 1 was repeated but substituting phenyl carbazate (77.3, 0.57 mole) for the ethyl carbazate and using phosgene (50 ml, 0.7 mole) in dry dichloromethane. 2-Phenoxycarbonylhydrazinecarbonyl chloride was isolated as impure solid (42 g, 54%) mp 76°-80° C. decomp., whose ir spectrum was consistent with the named compound being the major component.

Sources & evidence

ORD record
ord-090118ede4224ea595c3275c9fc20bf9
Source dataset
uspto-grants-1985_02
Patent number
US04501860

Reaction notes

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