Potassium Carbonate → HCID 58007510, compound

HRID 1094372Notes

Reaction equation

Br[C:2]1[S:6][C:5]([CH3:7])=[N:4][C:3]=1[CH3:8].[C:9]1([CH3:18])[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH2:17])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[CH3:7][C:5]1[S:6][C:2]([NH:17][CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([CH3:18])=[CH:10][CH:11]=2)=[C:3]([CH3:8])[N:4]=1

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of 5-bromo-2,4-dimethyl-1,3thiazole (1.00 g, 5.21 mmol) in DMSO (5 mL) was added 2-(p-tolyl)ethylamine (1.06 g, 7.81 mmol) and potassium carbonate (1.1 g, 7.9 mmol). The reaction mixture was stirred for 6 d at ambient temperature and for 2 d at 160° C. under a nitrogen atmosphere. After cooling to ambient temperature it was diluted with ethyl acetate (20 mL) and washed with aqueous sodium carbonate (saturated, 20 mL) and water (20 mL). Drying over sodium sulfate, concentration and purification by chromatography (SiO2, heptane:ethyl acetate=70:30 to 0:100) afforded the title compound (170 mg, 13%) as a light brown solid. MS m/e: 247.0 [M+H]+.

Workup

temperatureAfter cooling to ambient temperature it
washwashed with aqueous sodium carbonate (saturated, 20 mL) and water (20 mL)
dry with materialDrying over sodium sulfate, concentration and purification by chromatography (SiO2, heptane:ethyl acetate=70:30 to 0:100)

Sources & evidence

ORD record: ord-d9e3737e6e3f4acc9a9aff2d03ae995a
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133909B2

Reaction notes

Loading…