Ethanethiol → N-(1-ethylthio-2,2,2-trichloroethyl)-2-acetoxybenzamide

HRID 848057Notes

Reaction equation

HRID 848057 reaction equation
ClCCl.Cl[CH:5]([NH:10][C:11](=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][C:19](=[O:21])[CH3:20])[C:6]([Cl:9])([Cl:8])[Cl:7].[CH2:23]([SH:25])[CH3:24].C(N(CC)CC)C>O>[CH2:23]([S:25][CH:5]([NH:10][C:11](=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][C:19](=[O:21])[CH3:20])[C:6]([Cl:9])([Cl:8])[Cl:7])[CH3:24]

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 6344DichloromethaneHCID 8471TriethylamineHCID 129224872-[(1,2,2,2-Tetrachloroethyl)carbamoyl]phenyl acetate

Product 1

HCID 12940123N-(1-ethylthio-2,2,2-trichloroethyl)-2-acetoxybenzamideYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 ml of dichloromethane was added to 7.9 g of N-(1,2,2,2-tetrachloroethyl)-2-acetoxybenzamide. 1.3 g of ethyl mercaptan was add to the solution under stirring and then 2.0 g of triethylamine was added dropwise thereto at 10°-15° C. After effecting the reaction at room temperature for one hour, water was added thereto and the solution was allowed to stand. Then the dichloromethane layer was separated out, dried with unhydrous sodium sulfate and concentrated to obtain 7.0 g of N-(1-ethylthio-2,2,2-trichloroethyl)-2-acetoxybenzamide as white crystals.

Workup

  1. customat 10°-15° C
  2. customthe reaction at room temperature for one hour
  3. customThen the dichloromethane layer was separated out
  4. dry with materialdried with unhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c718cf4be1f148179ce53d8b9f976497
Source dataset
uspto-grants-1981_10
Patent number
US04294835

Reaction notes

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