3-Chloroaniline → Phenyl hydrogen (3-chlorophenyl)carbonimidate

HRID 359975Notes

Reaction equation

HRID 359975 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15]>CCOCC>[Cl:11][C:12]1[CH:13]=[C:14]([NH:15][C:2](=[O:3])[O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 15891Phenyl chloroformate

Product 1

HCID 232110Phenyl hydrogen (3-chlorophenyl)carbonimidate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1.56 g of phenyl chloroformate in 50 ml of ether was added dropwise to a stirred solution of 2.55 g of 3-chloroaniline in 35 ml of ether. The mixture was stirred for one hour at room temperature and then filtered. The filtrate was evaporated and the residue crystallized from hexane to yield phenyl N-(3-chlorophenyl)carbamate.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. customthe residue crystallized from hexane

Sources & evidence

ORD record
ord-d50174d69084488aad2ff70c1c431ef2
Source dataset
uspto-grants-1991_03
Patent number
US05003106

Reaction notes

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