Lithium Hydroxide → 2-(2,6-Dihydroxyphenyl)-4-thiazoleacetic Acid

HRID 260281Notes

Reaction equation

HRID 260281 reaction equation
OC1C=CC=CC=1C1SC=C(CC(O)=O)N=1.C([O:19][C:20](=[O:35])[CH2:21][C:22]1[N:23]=[C:24]([C:27]2[C:32]([OH:33])=[CH:31][CH:30]=[CH:29][C:28]=2[OH:34])[S:25][CH:26]=1)C.[Li+].[OH-]>>[OH:33][C:32]1[CH:31]=[CH:30][CH:29]=[C:28]([OH:34])[C:27]=1[C:24]1[S:25][CH:26]=[C:22]([CH2:21][C:20]([OH:35])=[O:19])[N:23]=1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 1357374432-(2-Hydroxyphenyl)-4-thiazoleacetic AcidHCID 1361470782-(2,6-Dihydroxyphenyl)-4-thiazoleacetic Acid Ethyl Ester

Product 1

HCID 1357374442-(2,6-Dihydroxyphenyl)-4-thiazoleacetic AcidYield 94%

Procedure

The procedure used for the preparation of 5a was repeated with 4b (805 mg, 2.89 mmol) and 2N LiOH (5.1 mL) to provide 5b (680 mg, 94%) as a yellowish solid, which was recrystallized from THF/hexane. mp 210° C. (dec); IR (KBr) 3540-2500 (br), 3256 (br), 1688, 1461, 1230 cm-1 ; 1H NMR (DMSO-d6) δ 3.78 (2H, s, CH2), 6.42 (2H, d, J=8.1 Hz, Ar), 7.08 (1H, t, J=8.1 Hz, Ar), 7.46 (1H, s), 12.21 (2H, s, OH), 12.47 (1H, br s, CO2H); FDMS m/z 251 (M+), 252 (M+ +1); Anal. Calcd for C11H9NO4S: C, 52.58; H, 3.61; N, 5.57. Found: C, 52.36; H, 3.57; N, 5.38.

Sources & evidence

ORD record
ord-cd3adb7c600346fb9a30be4b208d2507
Source dataset
uspto-grants-1996_06
Patent number
US05527792

Reaction notes

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