Ethyl 4-chloroacetoacetate → Ethyl 2-(2-(3-hydroxyphenyl)thiazol-4-yl)acetate

HRID 260030Notes

Reaction equation

HRID 260030 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2O)[S:9][CH:10]=1)[CH3:2].[OH:19]C1C=C(C(=S)N)C=CC=1.ClCC(=O)CC(OCC)=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:19])[CH:12]=2)[S:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 69484Ethyl 4-chloroacetoacetateHCID 27593433-Hydroxybenzene-1-carbothioamideHCID 1360263402-(2-Hydroxyphenyl)-4-thiazoleacetic Acid Ethyl Ester

Product 1

HCID 15336765Ethyl 2-(2-(3-hydroxyphenyl)thiazol-4-yl)acetateYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure used for the preparation of 4a was repeated with 3-hydroxybenzenecarbothioamide 3d (1.53 g, 10.0 mmol ) and ethyl 4 -chloroacetoacetate (1.65 g, 10.0 mmol) in dry THF (20 mL) to give 4d (2.04 g, 78%) as a white solid after chromatographic purification on silica gel (gradient EtOAc/hexane: 30-40%) and recrystallization from EtOAc/hexane. mp 95.5°-97.2° C.; IR (KBr) 3112, 1727, 1278 cm-1 ; 1H NMR (DMSO-d6) δ1.15 (3H, t, J=7.0 Hz, CH3), 3.81 (2H, s, CH2), 4.07 (2H, g, J=7.0 Hz, CH2), 6.81 (1H, d, J=7.3 Hz, Ar), 7.22-7.30 (3H, m, Ar), 7.46 (1H, s), 9.68 (1H, s, OH); FDMS m/z 263 (M+); Anal. Calcd for C13H13NO3S: C, 59.30; H, 4.98; N, 5.32. Found: C, 59.41; H, 4.91; N, 5.30.

Sources & evidence

ORD record
ord-776c2d7ccafb47a094acc7a03df96067
Source dataset
uspto-grants-1996_06
Patent number
US05525599

Reaction notes

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