Lithium Hydroxide → 2-(3-Hydroxyphenyl)-4-thiazoleacetic Acid

HRID 53578Notes

Reaction equation

HRID 53578 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:9][CH:10]=[C:11]([CH2:13][C:14]([OH:16])=[O:15])[N:12]=1.[Li+].[OH-:18]>>[OH:18][C:7]1[CH:2]=[C:3]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][C:14]([OH:16])=[O:15])[N:12]=2)[CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 1357374432-(2-Hydroxyphenyl)-4-thiazoleacetic Acid

Product 1

HCID 153367682-(3-Hydroxyphenyl)-4-thiazoleacetic AcidYield 99%

Procedure

The procedure used for the preparation of 5a was repeated with 4d (1.84 g, 7.00 mmol) and 2N LiOH (14.0 mL) to provide 5d (1.63 g, 99%) as a white solid, which was recrystallized from EtOAc/toluene. mp 172.0°-174.0° C.; IR (KBr) 3500-2400 (br), 3336 (br), 1689, 1442, 1276, 1231 cm-1 1H NMR (DMSO-d6) δ3.72 (2H, s, CH2), 6.81 (1H, d, J=7.4 Hz, Ar), 7.19-7.30 (3H m, Ar), 7.43 (1H, s), 9.67 (1H), br, s, OH), 12.40 (1H, br, s, CO2H); FDMS m/z 236 M+ +1); Anal. Calcd for C11H9NO3S: C, 56.14; H, 3.86; N, 5.95. Found: C, 56.11; H, 3.73; N, 5.80.

Sources & evidence

ORD record
ord-20669eada5264dd39a4592533bcf46d9
Source dataset
uspto-grants-1997_04
Patent number
US05620968

Reaction notes

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