2-Chlorocyclohexanone → 2-Amino-4,5,6,7-tetrahydrobenzothiazole

HRID 1372447Notes

Reaction equation

HRID 1372447 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[NH2:9][C:10]([NH2:12])=[S:11]>O1CCCC1>[S:11]1[C:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C:2]=2[N:9]=[C:10]1[NH2:12]

Participants

4

Reactant 2

HCID 132032-ChlorocyclohexanoneHCID 2723790Thiourea

Product 1

HCID 180462-Amino-4,5,6,7-tetrahydrobenzothiazoleYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 2-chlorocyclohexanone (200 mg, 1.5 mmol) and thiourea (114 mg, 1.5 mmol) in tetrahydrofuran (20 ml) was heated at reflux for 6 hours. The solution was concentrated under reduced pressure and the amine was purified by flash column chromatography using ethylacetate/hexane 1/1 as eluent to afford a colourless oil (169 mg, 74%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. concentrationThe solution was concentrated under reduced pressure
  4. customthe amine was purified by flash column chromatography

Sources & evidence

ORD record
ord-538808de17ae41b5aec37d76d111af6d
Source dataset
uspto-grants-2007_01
Patent number
US07157585B2

Reaction notes

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