Thiourea → Methyl 2-amino-4,5,6,7-tetrahydrobenzo[d]thiazole-7-carboxylate

HRID 1051913Notes

Reaction equation

HRID 1051913 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].[NH2:13][C:14]([NH2:16])=[S:15]>CCO>[NH2:16][C:14]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:13]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 83646766HCID 83646766, compound

Product 1

HCID 90303268Methyl 2-amino-4,5,6,7-tetrahydrobenzo[d]thiazole-7-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A soln. of methyl 2-bromo-3-oxocyclohexanecarboxylate (1.00 g, 4.25 mmol) and thiourea (0.36 g, 4.68 mmol) in EtOH (16 mL) was stirred at 70° 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 (0-1% MeOH/DCM) provided a yellow solid.

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 (0-1% MeOH/DCM)
  6. customprovided a yellow solid

Sources & evidence

ORD record
ord-0f2b967b38c24089b6ec9b682c0e2d1d
Source dataset
uspto-grants-2016_07
Patent number
US09388197B2

Reaction notes

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