Sodium Hydroxide → 6-methyl-pyrrolo[2,1-b]thiazole-7-carboxylic Acid

HRID 882789Notes

Reaction equation

HRID 882789 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:14])=[CH:8][N:9]2[CH:13]=[CH:12][S:11][C:10]=12)=[O:5])C.[OH-].[Na+]>CCO.O>[CH3:14][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[C:10]2[N:9]([CH:8]=1)[CH:13]=[CH:12][S:11]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 593168376-methyl-pyrrolo[2,1-b]thiazole-7-carboxylic Acid Ethyl Ester

Product 1

HCID 593168436-methyl-pyrrolo[2,1-b]thiazole-7-carboxylic Acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 6-methyl-pyrrolo[2,1-b]thiazole-7-carboxylic acid ethyl ester (7.29 mmol) and NaOH (10.9 mmol) in EtOH (11.8 mL) and water (11.8 mL) is heated to 75° C. for 3 d. 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=0.73 min; [M+H]+=182.0.

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-26204fddb1ef42fc80466f8a996726da
Source dataset
uspto-grants-2012_08
Patent number
US08236801B2

Reaction notes

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