Thiourea → Ethyl 2-amino-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylate

HRID 524414Notes

Reaction equation

HRID 524414 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[CH2:5]([O:7][C:8]([CH:10]1[CH2:15][CH2:14][C:13](=O)[CH:12](Br)[CH2:11]1)=[O:9])[CH3:6]>C(O)C>[CH2:5]([O:7][C:8]([CH:10]1[CH2:15][CH2:14][C:13]2[N:1]=[C:2]([NH2:4])[S:3][C:12]=2[CH2:11]1)=[O:9])[CH3:6]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 12917737Ethyl 3-bromo-4-oxocyclohexane-1-carboxylate

Product 1

HCID 15101101Ethyl 2-amino-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thiourea (0.672 g, 8.835 mmol) was taken in ethanol (30 mL). To this stirred solution was added 3-Bromo-4-oxo-cyclohexane carboxylic acid ethyl ester (2.2 g, 8.835 mmol). The reaction was refluxed for 2 hrs. The reaction mixture was allowed to cool to room temperature and ethanol was evaporated under reduced pressure, the residue was partitioned between water and ethyl acetate. The water layer was collected and basified using sat. sodium bicarbonate solution, extracted with ethyl acetate, the organic layer was washed with brine, dried over anhydrous sodium sulfate filtered and concentrated under reduced pressure to afford 2-Amino-4,5,6,7-tetrahydro-benzothiazole-6-carboxylic acid ethyl ester (1.6 g)

Workup

  1. temperatureThe reaction was refluxed for 2 hrs
  2. customethanol was evaporated under reduced pressure
  3. customthe residue was partitioned between water and ethyl acetate
  4. customThe water layer was collected
  5. extractionextracted with ethyl acetate
  6. washthe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8222c4bc41444d6ca27ce59fbd284668
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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