Ethyl 3-bromo-2-oxocyclohexanecarboxylate → Ethyl 2-amino-4,5,6,7-tetrahydrobenzthiazole-4-carboxyate hydrobromide

HRID 1394103

Reaction equation

HRID 1394103 reaction equation
[Br:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]1=O.[NH2:14][C:15]([NH2:17])=[S:16]>C(O)C>[BrH:1].[NH2:17][C:15]1[S:16][C:2]2[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]=2[N:14]=1

Participants

4

Reactant 2

HCID 121765Ethyl 3-bromo-2-oxocyclohexanecarboxylateHCID 2723790Thiourea

Product 1

HCID 87730500Ethyl 2-amino-4,5,6,7-tetrahydrobenzthiazole-4-carboxyate hydrobromide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol (50 mL) was added to ethyl 3-bromo-2-oxocyclohexane-carboxylate (50 g, 0.20 mol) and thiourea (15.3 g, 0.20 mol) and the reaction mixture was stirred for a period of 24 hours at room temperature under a blanket of nitrogen as inert gas. Following the removal of the solvent, ether (100 mL) was added to the residue. Following stirring for a period of 2 hours at room temperature, the suspension was filtered off and the solid matter was dried in vacuo. The product ethyl 2-amino-4,5,6,7-tetrahydrobenzthiazole-4-carboxyate hydrobromide was obtained in a yield of 58.6 g (corresponding to 95% of theory).

Workup

  1. customthe removal of the solvent, ether (100 mL)
  2. additionwas added to the residue
  3. stirringFollowing stirring for a period of 2 hours at room temperature
  4. filtrationthe suspension was filtered off
  5. customthe solid matter was dried in vacuo

Sources & evidence

ORD record
ord-9de07cbf27934ee28b6af45750699deb
Source dataset
uspto-grants-2008_03
Patent number
US07348347B2

Linked notes

Loading…