Thiourea → 4-Phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-2-amine

HRID 451399

Reaction equation

HRID 451399 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]1=O.[NH2:15][C:16]([NH2:18])=[S:17]>CCO>[C:8]1([CH:4]2[C:3]3[N:15]=[C:16]([NH2:18])[S:17][C:2]=3[CH2:7][CH2:6][CH2:5]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 127791292-Bromo-6-phenylcyclohexanone

Product 1

HCID 866566974-Phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-2-amineYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-6-phenyl-cyclohexanone (4.32 g, 17 mmol) and thiourea (1.18 g, 16 mmol) in EtOH (150 mL) was heated to reflux for 12 hours. The solvent was evaporated, diethyl ether was added to the residue and stirred at room temperature for 1 hour, the solid filtered off and washed with diethylether. The solid was dissolved in ethyl acetate and the organic phase was washed three times with sodium carbonate solution. The organic phase was dried over sodium sulfate, the solvent was evaporated to give the title compound as a white solid (3.46 g, 88%). MS ISP (m/e): 231.1 [(M+H)+].

Workup

  1. temperatureto reflux for 12 hours
  2. customThe solvent was evaporated
  3. additiondiethyl ether was added to the residue
  4. filtrationthe solid filtered off
  5. washwashed with diethylether
  6. dissolutionThe solid was dissolved in ethyl acetate
  7. washthe organic phase was washed three times with sodium carbonate solution
  8. dry with materialThe organic phase was dried over sodium sulfate
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b582739d2f4d49828f147136e948ad00
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Linked notes

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