Hydrochloric Acid → 2-Methyl-5-(thiazol-2-ylamino)phenol

HRID 1473969Notes

Reaction equation

Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[NH2:7][C:8]1[CH:9]=[C:10](C)[CH:11]=[C:12]([OH:14])[CH:13]=1.Cl.[CH3:17]CO>>[CH3:17][C:11]1[CH:10]=[CH:9][C:8]([NH:7][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)=[CH:13][C:12]=1[OH:14]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 764302-Bromothiazole

HCID 30186673-Amino-5-methylphenol

Product 1

HCID 866450292-Methyl-5-(thiazol-2-ylamino)phenolYield 74%

Conditions

Temperature: 90 °C

Procedure

Following the general procedure for the synthesis of 2-R-5-(thiazol-2-ylamino)phenol, 2-bromothiazole (0.27 mL, 3.05 mmol), 5-amino-3-methylphenol (188 mg, 1.5 mmol) and 37% HCl solution (0.26 mL, 3.05 mmol) in 10% aqueous EtOH solution (5 mL) was stirred at 90° C. for 24 h. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 1/1) in 74% yield (233 mg).

Sources & evidence

ORD record: ord-349dc3502ff949eb9b00a037f64d2998
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018209B2

Reaction notes

Loading…