Acetone → HCID 12940140, compound

HRID 848060Notes

Reaction equation

HRID 848060 reaction equation
[OH-].[Na+].Cl[CH:4]([NH:9][C:10](=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17]C(=O)C)[C:5]([Cl:8])([Cl:7])[Cl:6].CC(C)=O.[C:26]1([SH:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O>[C:26]1([S:32][CH:4]([NH:9][C:10](=[O:21])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[C:5]([Cl:6])([Cl:7])[Cl:8])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 129224872-[(1,2,2,2-Tetrachloroethyl)carbamoyl]phenyl acetate

Product 1

HCID 12940140HCID 12940140, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.3 g of a 20% acqueous NaOH solution was added dropwise to the mixture of 16.6 g of N-(1,2,2,2-tetrachloroethyl)-2-acetoxybenzamide, 70 ml of acetone and 5.3 g of phenyl mercaptan under stirring at 10°-15° C. The reaction was effected at room temperature for one hour. Water was added thereto, the dichloromethane layer was separated, and the solution was dried and concentrated. 100 ml of ethanol and 1.5 ml of 35% hydrochloric acid were added to the residue and the reaction was effected under reflux for two hours. The solvent was distilled off to obtain 14.5 g of N-(1-phenylthio-2,2,2-trichloroethyl)-2-hydroxybenzamide as white crystals.

Workup

  1. customthe dichloromethane layer was separated
  2. customthe solution was dried
  3. concentrationconcentrated
  4. addition100 ml of ethanol and 1.5 ml of 35% hydrochloric acid were added to the residue
  5. temperatureunder reflux for two hours
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-aca51e34939148f48da36d6deadfc7f0
Source dataset
uspto-grants-1981_10
Patent number
US04294835

Reaction notes

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