Propargyl bromide → Propargyl 2-chloro-4-trifluoromethyl-5-thiazolecarboxylate

HRID 746105Notes

Reaction equation

HRID 746105 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:11]([OH:13])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[CH2:14](Br)[C:15]#[CH:16].C(NC(C)C)(C)C>C(Cl)Cl>[Cl:1][C:2]1[S:3][C:4]([C:11]([O:13][CH2:16][C:15]#[CH:14])=[O:12])=[C:5]([C:7]([F:8])([F:10])[F:9])[N:6]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 7912DiisopropylamineHCID 132827432-Chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylic acid

Product 1

HCID 13670344Propargyl 2-chloro-4-trifluoromethyl-5-thiazolecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4.63 g (0.02 mole) of 2-chloro-4-trifluoromethyl-5-thiazolecarboxylic acid, 2.42 g (0.02 mole) of propargyl bromide, 2.59 g (0.02 mole) of diisopropylamine, and 50 ml. of methylene chloride was stirred for 16 hours. The methylene chloride solution was washed successively with diluted hydrochloric acid and saturated sodium bicarbonate, dried (MgSO4) and concentrated under reduced pressure. The residue was Kugelrohr distilled to give propargyl 2-chloro-4-trifluoromethyl-5-thiazolecarboxylate as a colorless liquid.

Workup

  1. washThe methylene chloride solution was washed successively with diluted hydrochloric acid and saturated sodium bicarbonate
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. distillationdistilled

Sources & evidence

ORD record
ord-e8024ad49db0450a98fee97d6f163137
Source dataset
uspto-grants-1986_07
Patent number
US04602454

Reaction notes

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