Ammonium dithiocarbamate → 4,5,6,7-Tetrahydro-1,3-benzothiazole-2-thiol

HRID 440317Notes

Reaction equation

HRID 440317 reaction equation
[C:1](=[S:4])([S-:3])[NH2:2].[NH4+].Br[CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]1=O>C(O)C>[SH:4][C:1]1[S:3][C:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[N:2]=1

Participants

4

Reactant 2

HCID 11083854Ammonium dithiocarbamateHCID 117897582-Bromocyclohexanone

Product 1

HCID 1785278174,5,6,7-Tetrahydro-1,3-benzothiazole-2-thiolYield 25.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ammonium dithiocarbamate (1.4 g, 12.4 mmol) in 25 mL of ethanol was added 2-bromocyclohexanone (2.2 g, 12.4 mmol). The reaction was stirred at rt overnight. The next morning the reaction was heated at 70° C. for 1 h. The solvent was removed under reduced pressure. The product was subjected to flash chromatography (3:1 hexane/ethyl acetate) to recover a yellow solid. Recrystallization from ethyl acetate afforded 0.54 g of 2-mercapto-4,5,6,7-tetrahydrobenzothiazole.

Workup

  1. temperatureThe next morning the reaction was heated at 70° C. for 1 h
  2. customThe solvent was removed under reduced pressure
  3. customto recover a yellow solid
  4. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-0ef5e8c1e9a04f3ab2cbd6135423fd6f
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

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