Dicyclohexylcarbodiimide → HCID 178500069, 화합물

HRID 743897노트

반응식

HRID 743897 반응식
C1(N=C=NC2CCCCC2)CCCCC1.OC1C2N=NNC=2C=CC=1.[CH3:26][O:27][C:28](=[O:34])[CH2:29][CH2:30][C:31]([O-])=O.[NH2:35][C:36]1[CH:37]=[C:38]([C:43]2[CH:50]=[CH:49][CH:48]=[CH:47][C:44]=2[C:45]#[N:46])[CH:39]=[CH:40][C:41]=1[NH2:42]>CN(C=O)C>[C:45]([C:44]1[CH:47]=[CH:48][CH:49]=[CH:50][C:43]=1[C:38]1[CH:39]=[CH:40][C:41]2[NH:42][C:31]([CH2:30][CH2:29][C:28]([O:27][CH3:26])=[O:34])=[N:35][C:36]=2[CH:37]=1)#[N:46]

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 6930703Mono-Methyl SuccinateHCID 21468845HCID 21468845, 화합물HCID 178418300HCID 178418300, 화합물

생성물 1

HCID 178500069HCID 178500069, 화합물수율 75.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Dicyclohexylcarbodiimide (0.11 moles, 2.26 g), hydroxybenzotriazole, (0.011 moles, 1.48 g) and monomethylsuccinate (0.011 moles, 1.45 g) were dissolved in 75 ml of DMF. 2-(3,4-Diaminophenyl)benzonitrile (0.01 moles, 2.0 g) was added. The reaction was stirred at room temperature for 48 hours The solvent was removed in vacuo. The residue was dissolved in ethyl acetate and washed thoroughly with brine. The ethyl acetate solution was dried over sodium sulfate and filtered. The solvent was removed. The residue was purified by HPLC on silica gel eluted with ethyl acetate. The material was dissolved in 400 ml toluene with 5 mg of p-toluenesulfonic acid and refluxed for 8 hours. The solvent was removed. The residue was purified by HPLC on silica gel eluted with ethyl acetate to yield 2.3 g of methyl 3-[5-(2-cyanophenyl)-1H-benzimidazole-2-yl]propionate. (MS).

후처리

  1. customwas removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed thoroughly with brine
  4. dry with materialThe ethyl acetate solution was dried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed
  7. customThe residue was purified by HPLC on silica gel
  8. washeluted with ethyl acetate
  9. dissolutionThe material was dissolved in 400 ml toluene with 5 mg of p-toluenesulfonic acid
  10. temperaturerefluxed for 8 hours
  11. customThe solvent was removed
  12. customThe residue was purified by HPLC on silica gel
  13. washeluted with ethyl acetate

출처 및 근거

ORD 기록
ord-aea734c5194e4b6c8dae3b256f2b7212
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556981

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