Dicyclohexylcarbodiimide → HCID 178418733, 화합물

HRID 9583

반응식

HRID 9583 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH2:12].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=S)=[C:16]([F:23])[CH:15]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[NH:12][C:3]3[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=3[N:1]=2)=[C:16]([F:23])[CH:15]=1

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 5208224-Trifluoromethyl-1,2-phenylenediamineHCID 27570034-Bromo-2-fluorophenylisothiocyanate

생성물 1

HCID 178418733HCID 178418733, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
45 °C

실험 절차

1,2-Diamino-5-trifluoromethylbenzene (0.50 g, 2.84 mmol) was diluted in dichloromethane (5 mL) and treated with 4-bromo-2-fluoro-phenylisothiocyanate (0.66 g, 2.84 mmol). The dark solution was stirred at 45° C. for 15 minutes, then 1,3-dicyclohexylcarbodiimide (0.44 g, 2.13 mmol) was added all at once. The reaction was heated in a 45° C. oil bath overnight, then cooled and concentrated at reduced pressure. The dark residue was diluted with ethyl acetate, and the organic layer was washed with water. The organic layer was dried (MgSO4) and concentrated in vacuo. The resulting dark brown oil was purified by flash chromatography on silica gel eluted on a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate. The title compound was collected as a light pink solid (0.60 g, 57%). 1H NMR (300 MHz, DMSO-d6) δ 11.3 (broad d, 1H), 9.87 (d, 1H), 7.50 (d, 2H), 7.61 (d, 1H), 7.55–7.41 (m, 3H), 7.35–7.30 (m, 1H); LC/MS m/z 356.2 (MH+), retention time 2.33 minutes.

후처리

  1. temperatureThe reaction was heated in a 45° C. oil bath overnight
  2. temperaturecooled
  3. concentrationconcentrated at reduced pressure
  4. additionThe dark residue was diluted with ethyl acetate
  5. washthe organic layer was washed with water
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting dark brown oil was purified by flash chromatography on silica gel
  9. washeluted on a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate
  10. customThe title compound was collected as a light pink solid (0.60 g, 57%)

출처 및 근거

ORD 기록
ord-66414de28ead4eef90b6009cd06980d8
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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