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

HRID 2049935Notes

Reaction equation

HRID 2049935 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-098da4297a1c4727a0d64efee7c7516d
Source dataset
uspto-grants-1980_04
Patent number
US04199506

Reaction notes

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