Hydrochloric Acid → N-(3-cyanophenyl)-N'-(4-cyanophenyl)cycloheptylurea

HRID 1059522

반응식

HRID 1059522 반응식
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[H-].[Na+].Br[CH2:24][CH2:25][CH2:26][CH2:27]Br.Cl.[CH3:30][CH2:31][CH2:32]CCC>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([N:9]([CH:24]2[CH2:32][CH2:31][CH2:30][CH2:27][CH2:26][CH2:25]2)[C:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[CH:17][CH:18]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 80561,4-DibromobutaneHCID 8058HexaneHCID 24758Sodium hydride2회HCID 3421111-(3-Cyanophenyl)-3-(4-cyanophenyl)urea

생성물 1

HCID 53652841N-(3-cyanophenyl)-N'-(4-cyanophenyl)cycloheptylurea

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

N-(3-Cyanophenyl)-N′-(4-cyanophenyl)urea (0.25 g, 0.95 mmol) was dissolved in DMF (2 ml) and added to a cooled slurry of sodium hydride (0.80 g, 2.0 mmol, hexane washed to remove the mineral oil) in dimethylformamide (25 ml) under a nitrogen atmosphere. After strirring for 15 min, 1,4-dibromobutane (0.25 g, 0.95 mmol) was added slowly. The reaction was stirred at 0° C. for 1 h and then allowed to warm to 75° C. for 3 h. To the reaction additional sodium hydride was added and the reaction was heated to 75° C. for an additional 6 h. The reaction was allowed to cool to ambient temperature, was poured into 1N HCl and extracted with ethyl acetate. The organic layer was washed with water and brine, then dried (MgSO4) and concentrated to give a viscous oil. The oil was purified by flash chromatography on silica gel eluting with methylene chloride: ethyl acetate 95:5 to give N-(3-cyanophenyl)-N′-(4-cyanophenyl)cycloheptylurea as an oil (0.075 gm 0.24 mmol); LRMS (M+H)+ m/z 317; 1H NMR (CDCl3): 7.7-7.45(m, 6H), 7.4(d, 2H), 3.82(m, 4H), 1.95(m, 4H).

후처리

  1. washwashed
  2. customto remove the mineral oil) in dimethylformamide (25 ml) under a nitrogen atmosphere
  3. temperatureto warm to 75° C. for 3 h
  4. temperaturethe reaction was heated to 75° C. for an additional 6 h
  5. temperatureto cool to ambient temperature
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customto give a viscous oil
  11. customThe oil was purified by flash chromatography on silica gel eluting with methylene chloride: ethyl acetate 95:5

출처 및 근거

ORD 기록
ord-093406ada7fa4f31987c6a17d583220b
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521614B1

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