2-Bromoethyl methyl ether → 5-(4-fluoro-benzyl)-3-(2-methoxyethyl)-3H-thiazol-2-ylidene-amine

HRID 255055Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 5-(4-fluoro-benzyl)-thiazol-2-ylamine (330 mg, 1.59 mmol) and 2-bromoethyl methyl ether (0.50 mL, 5.34 mmol) was heated to 85° C. and stirred for 12 hours. The mixture was cooled to ambient temperature, diluted with 20 mL of ethyl acetate and washed with saturated aqueous NaHCO3. The layers were separated and the aqueous phase was extracted with 2×20 mL ethyl acetate and the combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated. Purification by column chromatography (SiO2, 50% ethyl acetate in dichloromethane containing 0.5% Et3N) afforded 342 mg of the title compound: MS (LC/MS) m/z 267 (M+H)+.

Workup

temperatureThe mixture was cooled to ambient temperature
washwashed with saturated aqueous NaHCO3
customThe layers were separated
extractionthe aqueous phase was extracted with 2×20 mL ethyl acetate
dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customPurification by column chromatography (SiO2, 50% ethyl acetate in dichloromethane containing 0.5% Et3N)

Sources & evidence

ORD record: ord-c680b71a2f4b43e597cd2c59e49a9964
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875639B2

Reaction notes

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