Phenyl chloroformate → HCID 9794992, compound

HRID 1168159Notes

Reaction equation

HRID 1168159 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O>N1C=CC=CC=1>[CH3:11][C:8]1[CH:9]=[CH:10][C:2]2[N:1]=[C:13]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 762552-Amino-5-methylbenzoic acid

Product 1

HCID 9794992HCID 9794992, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-amino-5-methylbenzoic acid (1.0 g, 6.6 mmol) in pyridine (10 ml) was cooled to 0° C. and treated dropwise with phenyl chloroformate (3.3 ml, 26 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 16 h, after which time the pyridine was removed in vacuo. The residue was washed with water (20 ml) and dried in vacuo. Recrystallisation from toluene afforded the desired product as a pale brown solid (692 mg, 41%); δH (400 MHz, DMSO-D6) 2.40 (3H, s, CH3), 7.33-7.45 (3H, m, Ph), 7.48-7.55 (3H, m, Ph), 7.63 (1H, d, J 8, Ph), 7.89 (1H, s, Ph-H5); m/z (ES+) 254 (MH+).

Workup

  1. customafter which time the pyridine was removed in vacuo
  2. washThe residue was washed with water (20 ml)
  3. customdried in vacuo
  4. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-0c3fb3ede8ff4670869c1b61235603e4
Source dataset
uspto-grants-2003_09
Patent number
US06624161B2

Reaction notes

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