Ethanethiol → Ethyl 2-chloro-4-trifluoromethyl-5-thiazolecarbothioate

HRID 235544Notes

Reaction equation

HRID 235544 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:11](Cl)=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.C([SH:16])C.C(N([CH2:22][CH3:23])CC)C>CCOCC>[Cl:1][C:2]1[S:3][C:4]([C:11](=[S:16])[O:12][CH2:22][CH3:23])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 8471TriethylamineHCID 132827442-Chloro-4-trifluoromethyl-5-thiazolecarbonyl chloride

Product 1

HCID 54264203Ethyl 2-chloro-4-trifluoromethyl-5-thiazolecarbothioateYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

5.95 g (25.7 mmol) of 2-chloro-4-trifluoromethyl-5-thiazolecarbonyl chloride in 50 ml of anhydrous ether was added dropwise at 0° C. to a mechanically stirred mixture of ethyl mercaptan (2.1 ml, 28.3 mmol) and triethylamine (3 g, 30 mmol) in 100 ml of anhydrous ether. The workup for this reaction was the same as Example 1 except that the crude pale yellow oil was distilled in a Kugelrohr at 80° C./0.55 mm to yield a colorless oil, 5.59 g. This oil was crystallized from petroleum ether at -72° C. to yield ethyl 2-chloro-4-trifluoromethyl-5-thiazolecarbothioate as a white solid; 4.8 g (68% yield), mp 28°-32° C.

Workup

  1. distillationwas distilled in a Kugelrohr at 80° C./0.55 mm
  2. customto yield a colorless oil, 5.59 g
  3. customThis oil was crystallized from petroleum ether at -72° C.

Sources & evidence

ORD record
ord-dee11677e8964c7e80c2ea1e9ffffb9f
Source dataset
uspto-grants-1987_02
Patent number
US04640702

Reaction notes

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