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

HRID 255055

반응식

HRID 255055 반응식
[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

참가 물질

4

반응물 2

HCID 809722-Bromoethyl methyl etherHCID 7034795-(4-Fluoro-benzyl)-thiazol-2-ylamine

생성물 1

HCID 668590705-(4-fluoro-benzyl)-3-(2-methoxyethyl)-3H-thiazol-2-ylidene-amine수율 80.8%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
85 °C

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-c680b71a2f4b43e597cd2c59e49a9964
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875639B2

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