Acetone → HCID 12940163, compound

HRID 848062Notes

Reaction equation

HRID 848062 reaction equation
[C:1](Cl)(=[O:5])[O:2][CH2:3][CH3:4].[CH2:7]([S:11][CH:12]([NH:17][C:18](=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25])[C:13]([Cl:16])([Cl:15])[Cl:14])[CH2:8][CH2:9][CH3:10].CC(C)=O>C(N(CC)CC)C>[CH2:7]([S:11][CH:12]([NH:17][C:18](=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][C:1]([O:2][CH2:3][CH3:4])=[O:5])[C:13]([Cl:15])([Cl:16])[Cl:14])[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 180AcetoneHCID 10928Ethyl chloroformateHCID 12940146HCID 12940146, compound

Product 1

HCID 12940163HCID 12940163, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

13 g of ethyl chlorocarbonate was added to the mixture of 3.4 g of N-(1-n-butylthio-2,2,2-trichloroethyl)-2-hydroxybenzamide and 50 ml of acetone under stirring, and 1.0 g of triethylamine was added dropwise thereto at 0°-5° C. After effecting the reaction at room temperature for one hour, the solvent was distilled off under reduced pressure, 50 ml of water was added thereto and the solution was extracted with ethyl acetate. After washing the extract with water and drying, the solvent was distilled off to obtain 3.2 g of N-(1-n-butylthio-2,2,2-trichloroethyl)-2-ethoxycarbonyloxybenzamide as a brown oily substance. nD25 1.5350

Workup

  1. customat 0°-5° C
  2. customthe reaction at room temperature for one hour
  3. distillationthe solvent was distilled off under reduced pressure, 50 ml of water
  4. additionwas added
  5. extractionthe solution was extracted with ethyl acetate
  6. washAfter washing the
  7. extractionextract with water
  8. customdrying
  9. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-edfb54964f1d4ad2977e45a8425ce162
Source dataset
uspto-grants-1981_10
Patent number
US04294835

Reaction notes

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