Trichloroacetyl chloride → 2-Trichloroacetylmethylene-3-ethyl-benzothiazoline

HRID 1089404Notes

Reaction equation

HRID 1089404 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH3:12][C:13]1[S:14][C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[N+:17]=1[CH2:18][CH3:19].C(N(CC)CC)C.[Cl:31][C:32]([Cl:37])([Cl:36])[C:33](Cl)=[O:34]>C1(C)C=CC=CC=1>[Cl:31][C:32]([Cl:37])([Cl:36])[C:33]([CH:12]=[C:13]1[N:17]([CH2:18][CH3:19])[C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[S:14]1)=[O:34]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 84711Benzothiazolium, 3-ethyl-2-methyl-, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 543960172-Trichloroacetylmethylene-3-ethyl-benzothiazoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

10 g (28.6 mmol) of 2-methyl-3-ethyl-benzothiazolium p-toluenesulfonate are suspended in 150 ml of toluene, 6.8 g (67.2 mmol) of triethylamine are added and, at 5°-10° C. 6 g (33 mmol) of trichloroacetyl chloride, dissolved in a minor amount of toluene, are added dropwise. After three hours at room temperature, the ammonium salts are filtered off with suction, and the reaction solution is washed with water, dried over sodium sulfate and concentrated in vacuo. The product is caused to crystallize from the diisopropyl ether.

Workup

  1. additionare added dropwise
  2. filtrationthe ammonium salts are filtered off with suction
  3. washthe reaction solution is washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto crystallize from the diisopropyl ether

Sources & evidence

ORD record
ord-d6002d5007a34608ac0debe48ba35e09
Source dataset
uspto-grants-1990_10
Patent number
US04966828

Reaction notes

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