Dicyclohexylcarbodiimide → N-(4-bromophenyl)-6-(trifluoromethyl)-1H-benzimidazol-2-amine

HRID 9582

반응식

HRID 9582 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)=[CH:16][CH:15]=1.C1(N=C=NC2CCCCC2)CCCCC1>C1(C)C=CC=CC=1>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[NH:1][C:2]3[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=3[N:12]=2)=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 161334-Bromophenyl isothiocyanateHCID 5208224-Trifluoromethyl-1,2-phenylenediamine

생성물 1

HCID 21985819N-(4-bromophenyl)-6-(trifluoromethyl)-1H-benzimidazol-2-amine

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

1,2-Diamino-5-trifluoromethylbenzene (0.25 g, 1.42 mmol) was diluted in toluene (5 mL) and treated with 4-bromophenylisothiocyanate (0.30 g, 1.42 mmol). The dark solution was stirred at 100° C. for 15 minutes, then treated with 1,3-dicyclohexylcarbodiimide (0.44 g, 2.13 mmol). The reaction was maintained at 100° C. for 5 h. The reaction was concentrated and partitioned between ethyl acetate and water. The organic layer was separated, dried (MgSO4), and concentrated under reduced pressure. The dark brown oil was purified by flash chromatography on silica gel, eluting with a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate. The title compound was obtained as a light pink solid (0.50 g, 30%). 1H NMR (300 MHz, DMSO-d6) δ 11.3 (broad d, 1 H), 9.87 (d, 1 H), 7.50 (d, 2 H), 7.61 (d, 1 H), 7.55–7.42 (m, 3 H), 7.35–7.30 (m, 1 H); LC/MS m/z 356.2 (MH+), retention time 2.33 minutes.

후처리

  1. temperatureThe reaction was maintained at 100° C. for 5 h
  2. concentrationThe reaction was concentrated
  3. custompartitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe dark brown oil was purified by flash chromatography on silica gel
  8. washeluting with a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate

출처 및 근거

ORD 기록
ord-cbac10e252ac4979bdfd19db99c5bac4
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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