Water → N'-(2,4-difluorophenyl)-N-heptyl-N-[5-(4,5,6,7-tetrahydro-1H-benzimidazol-2-ylthio)pentyl]urea

HRID 486088

반응식

HRID 486088 반응식
[H-].[Na+].[N:3]1[C:4](=[S:12])[N:5]=[C:6]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=12.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[F:30])=[O:21].O>CN(C)C=O>[F:30][C:24]1[CH:25]=[C:26]([F:29])[CH:27]=[CH:28][C:23]=1[NH:22][C:20](=[O:21])[N:19]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][S:12][C:4]1[NH:5][C:6]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[N:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10342005N-(5-bromopentyl)-N'-(2,4-difluorophenyl)-N-heptylureaHCID 190975414,5,6,7-Tetrahydrobenzimidazol-2-thione

생성물 1

HCID 19097543N'-(2,4-difluorophenyl)-N-heptyl-N-[5-(4,5,6,7-tetrahydro-1H-benzimidazol-2-ylthio)pentyl]urea수율 18.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Part B. To a suspension of sodium hydride (0.099 g, 0.004 mol; washed free of the mineral oil with hexane) in N,N-dimethylformamide (15 ml) under a nitrogen atmosphere, cooled to 0°, 4,5,6,7-tetrahydrobenzimidazol-2-thione (0.50 g, 0.0033 mol) was added slowly. The reaction mixture was stirred for two hours and then a solution of N-(5-bromopentyl)-N'-(2,4-difluorophenyl)-N-heptyl urea (1.38 g, 0.0033 mol) in N,N-dimethylformamide (5 ml) was added. The reaction mixture was stirred at 0° for one hour, at ambient temperature for one hour, then was poured into water (50 ml) and extracted with ethyl acetate (2×50 ml). The combined organic extracts were washed with water and brine, then dried over magnesium sulfate and concentrated to give the crude product. The product was purified by flash chromatography on silica gel (250 ml) eluting with hexane: ethyl acetate (50:50::v:v) to give the title compound as a solid (0.30 g, 0.0006 mol), mp 98°-100°. 1H NMR (CDCl3) δ10.0-9.4 (bs,1H), 8.05-7.87 (m,1H), 6.91-6.75 (m,2H), 6.5-6.41 (d,1H,J=3.75 Hz), 3.42-3.2 (m,4H), 2.96-2.85 (t,2H,J=6.0 Hz), 2.61-2.45 (m,4H), 1.81-1.22 (m,20H), 0.88 (t,3H,J=6.5 Hz).

후처리

  1. washwashed free of the mineral oil with hexane) in N,N-dimethylformamide (15 ml) under a nitrogen atmosphere
  2. temperaturecooled to 0°
  3. stirringThe reaction mixture was stirred at 0° for one hour, at ambient temperature for one hour
  4. extractionextracted with ethyl acetate (2×50 ml)
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give the crude product
  9. customThe product was purified by flash chromatography on silica gel (250 ml)
  10. washeluting with hexane: ethyl acetate (50:50::v:v)

출처 및 근거

ORD 기록
ord-4144f0a05c8c41aea1df34a5f222875e
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05290801

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