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

HRID 260283Notes

Reaction equation

HRID 260283 reaction equation
OC1C=CC=CC=1C1SC=C(CC(O)=O)N=1.C([O:19][C:20](=[O:34])[CH2:21][C:22]1[N:23]=[C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=2)[S:25][CH:26]=1)C.[Li+].[OH-]>>[OH:33][C:29]1[CH:28]=[C:27]([C:24]2[S:25][CH:26]=[C:22]([CH2:21][C:20]([OH:34])=[O:19])[N:23]=2)[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 15336765Ethyl 2-(2-(3-hydroxyphenyl)thiazol-4-yl)acetateHCID 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) δ 3.72 (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-59560a2222e945f8928b7793a78ec204
Source dataset
uspto-grants-1996_06
Patent number
US05527792

Reaction notes

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