Thioacetamide → Methyl 2-methyl-4,5,6,7-tetrahydrobenzo[d]thiazole-7-carboxylate

HRID 1051915Notes

Reaction equation

HRID 1051915 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]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 83646766HCID 83646766, compound

Product 1

HCID 90303556Methyl 2-methyl-4,5,6,7-tetrahydrobenzo[d]thiazole-7-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  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 (0-40% EtOAc/Hept)
  6. 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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