Water → Phenyl (4-chloro-2-cyanophenyl)carbamate

HRID 1015894Notes

Reaction equation

HRID 1015894 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]#[N:5].CN(C1C=CC=CN=1)C.[C:20](Cl)(=[O:28])[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CC(N(C)C)=O>[Cl:10][C:7]1[CH:8]=[CH:9][C:2]([NH:1][C:20](=[O:28])[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:3]([C:4]#[N:5])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15891Phenyl chloroformateHCID 218852-DimethylaminopyridineHCID 800192-Amino-5-chlorobenzonitrile

Product 1

HCID 66877344Phenyl (4-chloro-2-cyanophenyl)carbamate

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

(Step 1) To a solution of 2-amino-5-chlorobenzonitrile (5.0 g) and dimethylaminopyridine (0.12 g) in dimethylacetamide (25 ml) was added dropwise phenyl chlorocarbonate (6.2 ml) at room temperature, and the mixture was stirred overnight. The reaction mixture was poured into water, and extracted twice with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5→3:7) to give phenyl (4-chloro-2-cyanophenyl)carbamate (7.04 g).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5→3:7)

Sources & evidence

ORD record
ord-84b34291be90421c8481871f2e49f0d4
Source dataset
uspto-grants-2011_07
Patent number
US07985863B2

Reaction notes

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