Dicyclohexylcarbodiimide → HCID 178500069、化合物

HRID 743897ノート

反応式

HRID 743897 の反応式
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]

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 6930703Mono-Methyl SuccinateHCID 21468845HCID 21468845、化合物HCID 178418300HCID 178418300、化合物

生成物 1

HCID 178500069HCID 178500069、化合物収率 75.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-aea734c5194e4b6c8dae3b256f2b7212
出典データセット
uspto-grants-1996_09
特許番号
US05556981

反応ノート

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