Hydrochloric Acid → 1,1-dimethyl-3-(pyrid-3-yl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxylic acid

HRID 2210597Notes

Reaction equation

HRID 2210597 reaction equation
[CH3:1][C:2]1([CH3:20])[S:6][CH:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[N:4]2[CH:13]=[CH:14][C:15]([C:16]([O:18]C)=[O:17])=[C:3]12.[OH-].[Na+].Cl>CO>[CH3:1][C:2]1([CH3:20])[S:6][CH:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[N:4]2[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[C:3]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19379134methyl 1,1-dimethyl-3-(pyrid-3-yl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxylate

Product 1

HCID 152927391,1-dimethyl-3-(pyrid-3-yl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 1,1-dimethyl-3-(pyrid-3-yl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxylate (1.1 g, 3.8 mmol), 1N aqueous NaOH (19 mmol), and methanol (40 mL) was refluxed for 17 hours. The reaction mixture was cooled to ambient temperature and taken to pH 4 with concentrated HCl. The thick solution was extracted twice with 9:1 CHCl3, isopropanol. The combined organic layers where washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give a yellow powder. The powder was triturated with ether to afford 1,1-dimethyl-3-(pyrid-3-yl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxylic acid as a pale-yellow powder.

Workup

  1. temperaturewas refluxed for 17 hours
  2. extractionThe thick solution was extracted twice with 9:1 CHCl3, isopropanol
  3. washThe combined organic layers where washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a yellow powder
  8. customThe powder was triturated with ether

Sources & evidence

ORD record
ord-c2591ce4b6df4dc09fb018f49a7fffa8
Source dataset
uspto-grants-1995_10
Patent number
US05459152

Reaction notes

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