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

HRID 560328Notes

Reaction equation

HRID 560328 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 aq. HCl (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 aq. HCl (1.0 M)
  3. filtrationThe obtained precipitate is filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-b74cb19e15304c0ab4014c031885a84f
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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