Water → HCID 11593905, compound

HRID 220734Notes

Reaction equation

HRID 220734 reaction equation
O.C([O:4][C:5]([CH:7]1[CH2:19][CH2:18][C:10]2[N:11]=[C:12]([NH:14][C:15](=[O:17])[CH3:16])[S:13][C:9]=2[CH2:8]1)=[O:6])C.[OH-].[Na+]>C(O)(=O)C>[C:15]([NH:14][C:12]1[S:13][C:9]2[CH2:8][CH:7]([C:5]([OH:6])=[O:4])[CH2:19][CH2:18][C:10]=2[N:11]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 117159592-Acetylamino-4,5,6,7-tetrahydro-benzothiazole-6-carboxylic acid ethyl ester

Product 1

HCID 11593905HCID 11593905, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 500 ml reactor equipped with mechanical stirrer, thermometer and condenser was loaded with 200 ml of water, 30 g of 2-acetylamino-4,5,6,7-tetrahydro-benzothiazole-6-carboxylic acid ethyl ester [(II), R1=ethyl, R═—NH—CO—CH3] and 52.2 g of 30% sodium hydroxide, keeping the temperature below 30° C.; during the addition the solid gradually solubilized until complete dissolution. After 2 hours, glacial acetic acid was dropwise added to pH=4.5-5.5; after approx. 1 hour the precipitated white solid was filtered, washed with 70 ml of water and dried to obtain 24.8 g of 2-acetylamino-4,5,6,7-tetrahydro-benzothiazole-6-carboxylic acid.

Workup

  1. customA 500 ml reactor equipped with mechanical stirrer
  2. customthe temperature below 30° C.
  3. additionduring the addition the solid
  4. dissolutiongradually solubilized until complete dissolution
  5. filtrationafter approx. 1 hour the precipitated white solid was filtered
  6. washwashed with 70 ml of water
  7. customdried

Sources & evidence

ORD record
ord-5b22140d39c24ee99e6710aece1b011a
Source dataset
uspto-grants-2012_06
Patent number
US08203002B2

Reaction notes

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