Sodium Carbonate → 8-[3-(5-chloro-1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one

HRID 46873

반응식

HRID 46873 반응식
CS(O[CH2:6][CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=2[NH:11][C:10]1=[O:19])(=O)=O.[C:20]1([N:26]2[C:30]3([CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[C:29](=[O:36])[NH:28][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Cl:18][C:16]1[CH:15]=[CH:14][C:13]2[N:9]([CH2:8][CH2:7][CH2:6][N:33]3[CH2:32][CH2:31][C:30]4([N:26]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH2:27][NH:28][C:29]4=[O:36])[CH2:35][CH2:34]3)[C:10](=[O:19])[NH:11][C:12]=2[CH:17]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 214248165-chloro-1,3-dihydro-2-oxo-2H-benzimidazole-1-propanol methanesulfonate

생성물 1

HCID 203855858-[3-(5-chloro-1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one수율 25%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4.9 parts of 5-chloro-1,3-dihydro-2-oxo-2H-benzimidazole-1-propanol methanesulfonate, 3.7 parts of 1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one, 3.4 parts of sodium carbonate and 90 parts of N,N-dimethylformamide is stirred and heated for 1 hour at 50°-60° C. The N,N-dimethylformamide is distilled off and the residue is taken up in water. The product is extracted with 4-methyl-2-pentanone. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 10% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue solidifies on triturating in 4-methyl-2-pentanone. The product is filtered off and crystallized twice: first from 2-propanol and then from a mixture of N,N-dimethylformamide and water, yielding 1.8 parts (25%) of 8-[3-(5-chloro-1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one; mp. 233.7° C.

후처리

  1. temperatureheated for 1 hour at 50°-60° C
  2. distillationThe N,N-dimethylformamide is distilled off
  3. extractionThe product is extracted with 4-methyl-2-pentanone
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and 10% of methanol as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customon triturating in 4-methyl-2-pentanone
  12. filtrationThe product is filtered off
  13. customcrystallized twice
  14. additionfirst from 2-propanol and then from a mixture of N,N-dimethylformamide and water

출처 및 근거

ORD 기록
ord-e5008fe0aff94439bbeef0212360b3e3
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04175129

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