Methyl chloroformate → (2-Cyclopropylcarbamoyl-phenyl)-carbamic acid methyl ester

HRID 896344Notes

Reaction equation

HRID 896344 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[C:4]([NH:6][CH:7]1[CH2:9][CH2:8]1)=[O:5].[CH3:14][O:15][C:16](Cl)=[O:17]>O>[CH3:14][O:15][C:16](=[O:17])[NH:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[C:4](=[O:5])[NH:6][CH:7]1[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 20600072-amino-N-cyclopropylbenzamide

Product 1

HCID 20814106(2-Cyclopropylcarbamoyl-phenyl)-carbamic acid methyl esterYield 99.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a slurry of 2-amino-N-cyclopropyl-benzamide (6.7 g, 38.1 mmol) in water was added KHCO3 (9.5 g, 95.1 mmol) followed by careful addition of methylchloroformate (5.88 ml, 76.2 mmol). The mixture was stirred for 12 h then the aqueous layer was extracted with EtOAc. The EtOAc extract was washed with 1N HCl then dried over MgSO4 and concentrated to give 8.9 g (99%) of (2-cyclopropylcarbamoyl-phenyl)-carbamic acid methyl ester.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. extractionThe EtOAc extract
  3. washwas washed with 1N HCl
  4. dry with materialthen dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3a9f0fe3b0a84313a213da891b71d62b
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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