Ethyl Acetate → 4-((((2-Methylphenyl)amino)carbonyl)amino)benzeneacetic acid

HRID 1797014Notes

Reaction equation

HRID 1797014 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[C:12]1([CH3:21])[C:13]([N:18]=[C:19]=[O:20])=[CH:14][CH:15]=[CH:16][CH:17]=1.CCOC(C)=O>CSC>[CH3:21][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1)=[O:20]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 145334-Aminophenylacetic acidHCID 691942-Tolyl isocyanate

Product 1

HCID 66052544-((((2-Methylphenyl)amino)carbonyl)amino)benzeneacetic acid

Reagents, catalysts & solvents 1

HCID 1068Dimethyl SulfideSolvent

Procedure

To a suspension of p-aminophenylacetic acid (56.8 g, 376 mmol) in DMS (150 mL) was added o-tolyl isocyanate (50 g, 376 mmol) dropwise. The reaction mixture was allowed to stir 1 h, and was poured into EtOAc (1.75 L) with stirring. The precipitate was collected and washed with EtOAc (400 mL) and MeCN (400 mL) to provide oMePUPA (80 g, 75%). ESMS M/z (M+H+) 285.1.

Workup

  1. stirringwith stirring
  2. customThe precipitate was collected
  3. washwashed with EtOAc (400 mL) and MeCN (400 mL)
  4. customto provide oMePUPA (80 g, 75%)

Sources & evidence

ORD record
ord-411a869691b14debad459c22f3d4aede
Source dataset
uspto-grants-2006_04
Patent number
US07034043B2

Reaction notes

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