2-Aminothiazole → Thiourea, N-(3-phenylpropyl)-N'-2-thiazolyl-

HRID 2257755ノート

反応式

HRID 2257755 の反応式
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]=[C:11]=[S:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C:14]1[S:15][CH:16]=[CH:17][N:18]=1.C(OCC)(=O)C>CN(C)C=O>[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]([NH:13][C:14]2[S:15][CH:16]=[CH:17][N:18]=2)=[S:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 21552-AminothiazoleHCID 8857Ethyl AcetateHCID 758153-Phenylpropyl isothiocyanate

生成物 1

HCID 3001100Thiourea, N-(3-phenylpropyl)-N'-2-thiazolyl-収率 16.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 3-phenylpropyl isothiocyanate (500 mg, 2.82 mmol) and 2-aminothiazole (300 mg, 3.0 mmol) in N,N-dimethylformamide (10 mL) was heated to 100° C. After 20 h, the reaction was cooled to room temperature and poured into ethyl acetate. The organic phase was washed with 1N hydrochloric acid, water (3×), and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The solid obtained was purified by flash chromatography on silica gel (1% ethyl acetate in dichloromethane) and then recrystallized from ethyl acetate to provide 129 mg of the title product. A second crop was recrystallized from 1:1 ethyl acetate/hexanes to provide another 110 mg of the title product. Total yield of the title product: 239 mg (30%) as an off-white solid. A sample was recrystallized again from ethyl acetate:

後処理

  1. washThe organic phase was washed with 1N hydrochloric acid, water (3×), and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe solid obtained
  6. customwas purified by flash chromatography on silica gel (1% ethyl acetate in dichloromethane)
  7. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-49e0bb418bbf447e99bd894422d2b3f3
出典データセット
uspto-grants-1997_08
特許番号
US05658907

反応ノート

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