Dimethylformamide → HCID 131722221, compound

HRID 1275435Notes

Reaction equation

HRID 1275435 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([Cl:10])[C:7](Cl)=[CH:6][C:5]=1C)(=[O:3])[CH3:2].[SH:13][CH2:14][C:15]([CH3:20])([CH3:19])[C:16]([OH:18])=[O:17].[CH3:21]N(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([S:13][CH2:14][C:15]([CH3:20])([CH3:19])[C:16]([OH:18])=[O:17])=[C:8]([Cl:10])[C:9]=1[CH3:21])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2641172,2-dimethyl-3-sulfanylpropanoic acidHCID 11138168HCID 11138168, compound

Product 1

HCID 131722221HCID 131722221, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100-ml three-necked round-bottomed flask was charged with 2.98 g (14.65 mmol) of 2-acetyl-4,5-dichlorotoluene, 1.72 g (12.84 mmol) of 3-mercaptopivalic acid and 15 ml of N,N-dimethylformamide under nitrogen atmosphere. Then, 3.04 g (22.00 mmol) of potassium carbonate was added. The reaction mixture was heated at 100~110° C. for 6 hours under nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature, and about 150 ml of water was added. The mixture was washed with chloroform twice, and an aqueous layer was neutralized and acidified with a 5 wt % hydrochloric acid aqueous solution. A precipitated gummy substance was extracted with ethyl acetate, and an organic layer was washed with a 1 wt % hydrochloric acid aqueous solution, with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to give 3.02 g (yield 78%) of 3-(4-acetyl-2-chloro-methylphenylthio)pivalic acid.

Workup

  1. temperatureThe reaction mixture was heated at 100~110° C. for 6 hours under nitrogen atmosphere
  2. washThe mixture was washed with chloroform twice
  3. extractionA precipitated gummy substance was extracted with ethyl acetate
  4. washan organic layer was washed with a 1 wt % hydrochloric acid aqueous solution, with water and with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e7d8c0759c874612adf70846e156c823
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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