Water → HCID 14810936, compound

HRID 1014034Notes

Reaction equation

HRID 1014034 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:23])[O:21][CH3:22].O>CN(C)C(=O)C>[Cl:10][C:7]1[CH:8]=[CH:9][C:2]([NH:1][C:20](=[O:23])[O:21][CH3:22])=[C:3]([C:4]#[N:5])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 218852-DimethylaminopyridineHCID 800192-Amino-5-chlorobenzonitrile

Product 1

HCID 14810936HCID 14810936, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

(Step 1) To a solution of 2-amino-5-chlorobenzonitrile (1.95 g) and dimethylaminopyridine (20.3 mg) in N,N-dimethylacetamide (15 ml) was added dropwise methyl chlorocarbonate (3.5 ml) at room temperature, and the mixture was stirred at 90° C. for 5 hr. The mixture was allowed to cool to room temperature, poured into water, and extracted 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=3:20-1:4) to give methyl (4-chloro-2-cyanophenyl)carbamate (1.21 g) as a white solid.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:20-1:4)

Sources & evidence

ORD record
ord-4328808e363c40c987ae14bd6fe51158
Source dataset
uspto-grants-2011_07
Patent number
US07982044B2

Reaction notes

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