Lithium Hydroxide → 2-Chloro-1,3-thiazole-4-carboxylic acid
Reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([Cl:11])[S:9][CH:10]=1)=[O:5])C.[Li+].[OH-]>C1COCC1>[Cl:11][C:8]1[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a stirred solution of 2-chlorothiazole-4-carboxylic acid ethyl ester (20.49 g, 0.107 mol) in THF (180 mL) at RT, a 1M solution of LiOH (aq) (160 mL, 0.160 mol) was added. The resulting solution was heated to 65° C. for 1 h. The solvent was evaporated in vacuo. The residue was treated with brine (100 mL) and acidified to pH 1 with 1M HCl (aq). The precipitate was filtered off, washed with H2O (2×50 mL) and Et2O (2×50 mL) and dried in a vacuum oven at 60° C. for 62 h to yield the title compound as a pale yellow solid. MS m/z: 164.1 (M+H). Calc'd. for C4H2ClNO2S-163.58.
Workup
- customThe solvent was evaporated in vacuo
- additionThe residue was treated with brine (100 mL)
- filtrationThe precipitate was filtered off
- washwashed with H2O (2×50 mL) and Et2O (2×50 mL)
- customdried in a vacuum oven at 60° C. for 62 h
Sources & evidence
- ORD record
- ord-8e40e67514ac4802afd2784a6549cca7
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07196104B2
Reaction notes
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