Hydrochloric Acid → 2-Cyclopropyl-1,3-thiazole-4-carboxylic acid

HRID 460212Notes

Reaction equation

HRID 460212 reaction equation
[CH:1]1([C:4]2[S:5][CH:6]=[C:7]([C:9]([O:11]CC)=[O:10])[N:8]=2)[CH2:3][CH2:2]1.Cl>C1COCC1.CO.O>[CH:1]1([C:4]2[S:5][CH:6]=[C:7]([C:9]([OH:11])=[O:10])[N:8]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18771956Ethyl 2-cyclopropylthiazole-4-carboxylate

Product 1

HCID 187718162-Cyclopropyl-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a mixture of ethyl 2-cyclopropyl-thiazole-4-carboxylate (0.443 g, 2.249 mmol) and LiOH monohydrate (0.472 g, 11.243 mmol) was added a mixture of THF/MeOH/H2O (3:1:1, 50 mL). The reaction was stirred at RT for 24 h. The solution was acidified by addition of conc. HCl (0.1 mL) and the volatiles were removed. Remaining aqueous solution was extracted with EtOAc (3×20 mL). The combined organic layers were dried over Na2SO4 and evaporated to dryness. MS m/z: 169.9 (M+H) Calc'd. for C7H7NO2S-170.0.

Workup

  1. additionwas added
  2. customthe volatiles were removed
  3. extractionRemaining aqueous solution was extracted with EtOAc (3×20 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-f8408776d12a47f19772f57013c5cee6
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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