Methyl 2-amino-4-chloro-5-iodobenzoate → 4-Chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-iodo-benzoic acid methyl ester

HRID 1857630Notes

Reaction equation

HRID 1857630 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([I:10])[C:7]([Cl:11])=[CH:6][C:5]=1[NH2:12].[CH3:14][C:15]1[CH:16]=[C:17]([CH2:22][C:23](Cl)=[O:24])[CH:18]=[C:19]([CH3:21])[CH:20]=1>>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([I:10])[C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:23](=[O:24])[CH2:22][C:17]1[CH:16]=[C:15]([CH3:14])[CH:20]=[C:19]([CH3:21])[CH:18]=1

Participants

3

Reactant 2

HCID 10852539Methyl 2-amino-4-chloro-5-iodobenzoateHCID 15895699(3,5-Dimethylphenyl)acetyl chloride

Product 1

HCID 540909164-Chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-iodo-benzoic acid methyl ester

Conditions

Temperature
75 °C

Procedure

To a solution of 2-amino-4-chloro-5-iodo-benzoic acid methyl ester (2.26 g in 25 mL dichloroethane) was added (3,5-dimethylphenyl) acetyl chloride (1.2 g in 15 mL dichloroethane) and the mixture heated to 75° C. on an oil bath. After 3 hours, the reaction was cooled and the solvent removed in vacuo. The title compound was isolated by crystallization from methanol (2.7 g).

Workup

  1. temperaturethe reaction was cooled
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-135bf16af6e24199a6363aebf26854a5
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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