Thiobenzamide → Methyl 2-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazole-7-carboxylate

HRID 1051917Notes

Reaction equation

HRID 1051917 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]([NH2:21])(=[S:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCO>[C:14]1([C:13]2[S:20][C:2]3[CH:3]([C:9]([O:11][CH3:12])=[O:10])[CH2:4][CH2:5][CH2:6][C:7]=3[N:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 683563ThiobenzamideHCID 83646766HCID 83646766, compound

Product 1

HCID 90303482Methyl 2-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazole-7-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A soln. of methyl 2-bromo-3-oxocyclohexanecarboxylate (100 mg, 0.43 mmol) and thiobenzamide (64 mg, 0.47 mmol) in EtOH (2 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 (2-15% EtOAc/Hept) provided a yellow oil.

Workup

  1. customSubsequently, the mixture was quenched with aq. sat. NaHCO3
  2. extractionextracted with EtOAc
  3. washlayers were washed with brine
  4. dry with materialdried over MgSO4
  5. customPurification by means of CC (2-15% EtOAc/Hept)
  6. customprovided a yellow oil

Sources & evidence

ORD record
ord-6e769148e7034c299eae2b771e341106
Source dataset
uspto-grants-2016_07
Patent number
US09388197B2

Reaction notes

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