Sodium Hydroxide → Pyrrolo[2,1-b][1,3]thiazole-7-carboxylic acid

HRID 2064783Notes

Reaction equation

HRID 2064783 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][N:9]2[CH:13]=[CH:12][S:11][C:10]=12)=[O:5])C.[OH-].[Na+]>CO.O>[S:11]1[CH:12]=[CH:13][N:9]2[CH:8]=[CH:7][C:6]([C:4]([OH:5])=[O:3])=[C:10]12

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23643153pyrrolo[2,1-b]thiazole-7-carboxylic Acid Ethyl Ester

Product 1

HCID 59316832Pyrrolo[2,1-b][1,3]thiazole-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of pyrrolo[2,1-b]thiazole-7-carboxylic acid ethyl ester (5.12 mmol) and sodium hydroxide (7.68 mmol) in MeOH (5.8 mL) and water (5.8 mL) is heated to 55° C. for 23 h. The mixture is concentrated in vacuo and made acidic by addition of hydrochloric acid (1.0 M). The obtained precipitate is filtered off and dried in vacuo to give the desired product. LC-MS: tR=0.87 min; [M+H]+=168.0.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. additionmade acidic by addition of hydrochloric acid (1.0 M)
  3. filtrationThe obtained precipitate is filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-fc676d513fd94280b75ad5668ca4eff5
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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