Thioacetamide → Methyl 2-methyl-4,5,6,7-tetrahydrobenzo[d]thiazole-7-carboxylate
Reaction equation
Br[CH:2]1[C:7](=O)[CH2:6][CH2:5][CH2:4][CH:3]1[C:9]([O:11][CH3:12])=[O:10].[C:13]([NH2:16])(=[S:15])[CH3:14]>CCO>[CH3:14][C:13]1[S:15][C:2]2[CH:3]([C:9]([O:11][CH3:12])=[O:10])[CH2:4][CH2:5][CH2:6][C:7]=2[N:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A soln. of methyl 2-bromo-3-oxocyclohexanecarboxylate (150 mg, 0.64 mmol) and thioacetamide (53 mg, 0.70 mmol) in EtOH (3 mL) was stirred at 85° C. overnight. Subsequently, the mixture was quenched with aq. sat. NaHCO3 and extracted with EtOAc. The comb. org. layers were washed with brine, dried over MgSO4, and conc. in vacuo. Purification by means of CC (0-40% EtOAc/Hept) provided a yellow oil.
Workup
- customSubsequently, the mixture was quenched with aq. sat. NaHCO3
- extractionextracted with EtOAc
- washlayers were washed with brine
- dry with materialdried over MgSO4
- customPurification by means of CC (0-40% EtOAc/Hept)
- customprovided a yellow oil
Sources & evidence
- ORD record
- ord-ec4bd327b123450fbabae25352b1e6e8
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388197B2
Reaction notes
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