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

HRID 18680Notes

Reaction equation

HRID 18680 reaction equation
O.Br.[CH2:3]([O:5][C:6]([CH:8]1[CH2:17][CH2:16][C:11]2[N:12]=[C:13]([NH2:15])[S:14][C:10]=2[CH2:9]1)=[O:7])[CH3:4]>CO>[CH2:3]([O:5][C:6]([CH:8]1[CH2:17][CH2:16][C:11]2[N:12]=[C:13]([NH2:15])[S:14][C:10]=2[CH2:9]1)=[O:7])[CH3:4]

Participants

4

Reactant 2

HCID 962WaterHCID 86614358Ethyl 2-amino-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylate hydrobromide

Product 1

HCID 15101101Ethyl 2-amino-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylateYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2 liter reactor equipped with mechanical stirrer, thermometer and condenser was loaded with 600 ml of water, 110 g of 2-amino-4,5,6,7-tetrahydro-benzothiazole-6-carboxylic acid ethyl ester hydrobromide [(III), R1=ethyl] and 120 ml of methanol. The mixture was refluxed and hot filtered on a Celite bed. The resulting solution was added with a solution of 32 g of sodium bicarbonate in 300 ml of water (final pH=7-8). After 2 hours at room temperature, the precipitated white solid was filtered, washed with 100 ml of water and dried to obtain 72 g of the title product.

Workup

  1. customA 2 liter reactor equipped with mechanical stirrer
  2. temperatureThe mixture was refluxed
  3. filtrationhot filtered on a Celite bed
  4. additionThe resulting solution was added with a solution of 32 g of sodium bicarbonate in 300 ml of water (final pH=7-8)
  5. filtrationthe precipitated white solid was filtered
  6. washwashed with 100 ml of water
  7. customdried

Sources & evidence

ORD record
ord-1709020a78814d1881650ff883281b13
Source dataset
uspto-grants-2010_06
Patent number
US07741490B2

Reaction notes

Loading…