HCID 178418395, compound → HCID 178527778, compound

HRID 1589712

Reaction equation

HRID 1589712 reaction equation
CCCCCCCCCCCCCCCCC=C.[S:19][Cl:20].[SH:21][C:22]1[S:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1(C)C=CC=CC=1>[S:19][Cl:20].[SH:21][C:22]1[S:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1

Participants

5

Reactant 2

HCID 178418395HCID 178418395, compoundHCID 178443003HCID 178443003, compound

Product 1

HCID 178527778HCID 178527778, compoundYield 397.2%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

278.4 gm of the product of Example 1 (0.4 mol.), 133.8 gm of 2-mercaptobenzothiazole (0.8 mol.), 8 gm of Aliquat 336 (phase transfer catalyst obtained from Aldrich Chemical Company: tricaprylylmethyl ammonium chloride), 200 ml caustic solution (32 gm sodium hydroxide dissolved in 200 ml water), and 400 ml toluene were mixed in a 2-liter reactor. The reactants were stirred under reflux for six hours, and then cooled to ambient temperature. The aqueous phase was separated, and the organic phase was twice washed with 400 ml of water. Thereafter, toluene was removed by vacuum distillation leaving a dark fluid as the desired product (373 gm). It was further purified by hot filtration through Super-Cel.

Workup

  1. temperatureunder reflux for six hours
  2. customThe aqueous phase was separated
  3. washthe organic phase was twice washed with 400 ml of water
  4. customThereafter, toluene was removed by vacuum distillation

Sources & evidence

ORD record
ord-6fe259680bc6441d8d271f5006828699
Source dataset
uspto-grants-1993_04
Patent number
US05199960

Linked notes

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