Hydrochloric Acid → 2-Chloroacetylamino-5-ethoxycarbonyl-4,6-dimethylbenzoic acid

HRID 1680836Notes

Reaction equation

HRID 1680836 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:7]([CH3:17])[C:3]=1[C:4]([OH:6])=[O:5].N1C=CC=CC=1.[Cl:24][CH2:25][C:26](Cl)=[O:27].Cl>C1C=CC=CC=1>[Cl:24][CH2:25][C:26]([NH:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:7]([CH3:17])[C:3]=1[C:4]([OH:6])=[O:5])=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 126858402-Amino-5-ethoxycarbonyl-4,6-dimethylbenzoic acid

Product 1

HCID 129124362-Chloroacetylamino-5-ethoxycarbonyl-4,6-dimethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To an ice-cooled mixture consisting of 0.8 g of 2-amino-5-ethoxycarbonyl-4,6-dimethylbenzoic acid, 20 ml of dry benzene, and 0.5 ml of pyridine was added dropwise with stirring a solution of 0.4 ml of chloroacetyl chloride in 5 ml of benzene. The mixture was stirred overnight and then, shaken with dilute hydrochloric acid. The layers were separated. The aqueous layer was extracted with ethyl acetate, and the combined organic extracts were washed with water, dried over sodium sulfate, and evaporated. The residue was recrystallized from ethyl ether/n-hexane to give 0.65 g of 2-chloroacetylamino-5-ethoxycarbonyl-4,6-dimethylbenzoic acid (m.p. 124°-125° C.).

Workup

  1. additionwas added dropwise
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was recrystallized from ethyl ether/n-hexane

Sources & evidence

ORD record
ord-ed721349c55e4a99ada2ecf3e4faa220
Source dataset
uspto-grants-1981_06
Patent number
US04276295

Reaction notes

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