tert-Butyl mercaptan → HCID 54548855, compound

HRID 1979805Notes

Reaction equation

HRID 1979805 reaction equation
Cl[CH:2]=[C:3]([Cl:7])[C:4](=[O:6])[CH3:5].[C:8]([SH:12])([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C>C(OCC)C>[Cl:7][C:3]([C:4](=[O:6])[CH3:5])=[CH:2][S:12][C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 8471TriethylamineHCID 534251373,4-Dichlorobut-3-en-2-one

Product 1

HCID 54548855HCID 54548855, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
5 °C

Procedure

To a mixture of 20.85 g (0.15 mole) 1,2-dichloro-1-buten-3-one and 13.53 g (0.15 mole) t-butylmercaptan in 300 ml ethyl ether, cooled to 5° C. is added dropwise 15.18 g (0.15 mole) triethylamine in 50 ml ether. After stirring at room temperature for 18 hours the mixture is heated at reflux for 2 days. The resulting mixture is washed with water, brine and the organic layer dried over magnesium sulfate. Evaporation of ether affords a brown oil which is distilled in vacuo to yield 17.56 g of product as a light yellow liquid, B.P. 75° (0.1 mm) which crystallized upon standing, M.P. 73° C. Mass spectrum (m/e) 192 (molecular ion), 138, 136.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 days
  3. washThe resulting mixture is washed with water, brine
  4. dry with materialthe organic layer dried over magnesium sulfate
  5. customEvaporation of ether
  6. customaffords a brown oil which
  7. distillationis distilled in vacuo

Sources & evidence

ORD record
ord-e2f1e286b6ce4938839c60a77bcdf552
Source dataset
uspto-grants-1984_11
Patent number
US04482723

Reaction notes

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