Sulfuric Acid → HCID 12774585, compound

HRID 895024Notes

Reaction equation

HRID 895024 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]([CH3:14])[CH3:13])[C:9](O)=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[SH-].[Na+].[S:30](=O)(=O)(O)O>CN(C)C=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]([CH3:14])[CH3:13])[C:9](=[O:10])[SH:30])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 16197Benzeneacetic acid, 4-chloro-alpha-(1-methylethyl)-HCID 28015Sodium hydrosulfide

Product 1

HCID 12774585HCID 12774585, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Three grams (14.1 mmol) of 2-(4-chlorophenyl)-3-methylbutanoic acid is dissolved in approximately 50 ml of dry dimethylformamide, after which 1.43 g (14.1 mmol) of triethylamine is added in one portion. The solution is cooled to 0° and 1.59 g (14.1 mmol) of ethyl chloroformate is slowly added over 30 seconds. After 0.5 hour 3.15 g (28.2 mmol) of sodium hydrosulfide is added. The mixture is stirred overnight at room temperature. The reaction mixture is then poured into 150 ml of water and adjusted to pH 3 with 5% aqueous sulfuric acid. Extraction with 50 ml methylene chloride (3×) is followed by drying and stripping. Dimethylforamide is still present, so the product is taken up in ether and washed with 200 ml of water, dried and stripped to yield 2-(4-chlorophenyl)-3-methylbutanethioic S-acid.

Workup

  1. temperatureThe solution is cooled to 0°
  2. extractionExtraction with 50 ml methylene chloride (3×)
  3. customby drying
  4. washwashed with 200 ml of water
  5. customdried

Sources & evidence

ORD record
ord-4a0c85c9847347a49372c30d4f03ed0a
Source dataset
uspto-grants-1981_08
Patent number
US04285954

Reaction notes

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