Dimethylformamide → HCID 86632549, compound

HRID 2427068Notes

Reaction equation

HRID 2427068 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[C:9]([Cl:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CN(C)C=O.[Cl:18]N1C(=O)CCC1=O>O>[NH2:1][C:2]1[C:10]([CH3:11])=[C:9]([Cl:12])[C:8]([Cl:18])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 8274632-Amino-4-chloro-3-methylbenzoic acid

Product 1

HCID 86632549HCID 86632549, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 0.34 g of 2-amino-4-chloro-3-methylbenzoic acid and 10 ml of N,N-dimethylformamide was added 0.26 g of N-chlorosuccinimide at room temperature, and the mixture was stirred at room temperature for 5 hours. After 30 ml of water was poured into the reaction mixture, the mixture was extracted with ethyl acetate three times. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 0.22 g of 2-amino-4,5-dichloro-3-methylbenzoic acid of the formula:

Workup

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-538548796c7c4edd95110a7d09a7ff22
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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