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

HRID 2257755노트

반응식

HRID 2257755 반응식
[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

참가 물질

5

반응물 3

HCID 21552-AminothiazoleHCID 8857Ethyl AcetateHCID 758153-Phenylpropyl isothiocyanate

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-49e0bb418bbf447e99bd894422d2b3f3
출처 데이터셋
uspto-grants-1997_08
특허 번호
US05658907

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