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

HRID 255055ノート

反応式

HRID 255055 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-c680b71a2f4b43e597cd2c59e49a9964
出典データセット
uspto-grants-2011_01
特許番号
US07875639B2

反応ノート

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