Hydrochloric Acid → 2-Thiazolecarboxylic acid, 4-(1-methylethyl)-

HRID 1443423Notes

Reaction equation

HRID 1443423 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([C:9]([O:11]CC)=[O:10])[S:7][CH:8]=1)([CH3:3])[CH3:2].[OH-].[Li+].Cl>C1COCC1.CO>[CH:1]([C:4]1[N:5]=[C:6]([C:9]([OH:11])=[O:10])[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 10821861Ethyl 4-isopropylthiazole-2-carboxylate

Product 1

HCID 224993072-Thiazolecarboxylic acid, 4-(1-methylethyl)-

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-isopropylthiazole-2-carboxylate (9.1 g, 46 mmol) in THF (100 ml) and MeOH (30 ml) was added a solution of lithium hydroxide (1.16 g, 48.5 mmol) and the mixture was stirred for two days at room temperature. The mixture was acidified with 2M hydrochloric acid and extracted four times with diethyl ether. The organic phase was dried with sodium sulfate and evaporated under reduced pressure. Yield: 7.1 g, 90%.

Workup

  1. extractionextracted four times with diethyl ether
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-30d0ee3d77a347bea9669d4b631bdbe1
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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