Acetic Anhydride → HCID 20363160, compound

HRID 1679514Notes

Reaction equation

HRID 1679514 reaction equation
[Cl:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]([CH3:23])([CH3:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)[C:3]([NH2:5])=[O:4].[C:24](OC(=O)C)(=[O:26])[CH3:25]>C1(C)C=CC=CC=1.S(=O)(=O)(O)O>[C:24]([NH:5][C:3](=[O:4])[CH:2]([Cl:1])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]([CH3:23])([CH3:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)(=[O:26])[CH3:25]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 20462537HCID 20462537, compound

Product 1

HCID 20363160HCID 20363160, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 1140TolueneSolvent

Procedure

In 3 ml of toluene is dissolved 2.8 g of 2-chloro-3-[4-(2,2-dimethyl-2-phenylethyloxy)phenyl]propionamide, and to the solution are added 1.0 g of acetic anhydride and one drop of concentrated sulfuric acid. The mixed solution is stirred under heating at 100° to 110° C for 1.5 hour. After cooling, the solvent is distilled off and water is added to the residue. The resulting crystals are recrystallized from ethanol to give 2.8 g of N-acetyl-2-chloro-3-[4-(2,2-dimethyl-2-phenylethyloxy)phenyl]propionamide.

Workup

  1. temperatureunder heating at 100° to 110° C for 1.5 hour
  2. temperatureAfter cooling
  3. distillationthe solvent is distilled off
  4. additionwater is added to the residue
  5. customThe resulting crystals are recrystallized from ethanol

Sources & evidence

ORD record
ord-7e78cd45a1ab456b9a765865e56290b6
Source dataset
uspto-grants-1978_03
Patent number
US04080505

Reaction notes

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