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Methyl Isobutyl Ketone → 5-Chloro-1,3-dihydro-2H-benzimidazol-2-one

HRID 1833677
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HRID 1833677 반응식
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6](C3CCNCC3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C.BrCCCN1C2C=CC=CC=2N=N1>O>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 3732348HCID 3732348, 화합물

생성물 1

HCID 2231315-Chloro-1,3-dihydro-2H-benzimidazol-2-one

시약·촉매·용매 1

HCID 962Water용매
2회

실험 절차

A mixture of 5 parts of 5-chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 3.7 parts of sodium carbonate and 200 parts of 4-methyl-2-pentanone is stirred and refluxed with water-separator. Then there are added 4.8 parts of 1-(3-bromopropyl)-1H-benzotriazole and stirring is continued overnight at reflux temperature. The reaction mixture is cooled, water is added and the undissolved product is filtered off and set aside. The organic phase is separated from the filtrate, dried, filtered and evaporated. The residue is combined with the undissolved product (see above) and purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 4-methyl-2-pentanone, yielding 2 parts (25%) of 1-{1-[3-H-benzotriazol-1-yl)propyl]-4-piperidinyl}-5-chloro-1,3-dihydro-2H-benzimidazol-2-one; mp. 203.4° C.

후처리

  1. stirringstirring
  2. temperatureat reflux temperature
  3. temperatureThe reaction mixture is cooled
  4. filtrationthe undissolved product is filtered off
  5. customThe organic phase is separated from the filtrate
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. custompurified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated
  13. customThe residue is crystallized from 4-methyl-2-pentanone

출처 및 근거

ORD 기록
ord-2321b7d8914b42be81f522b7af9d2cca
출처 데이터셋
uspto-grants-1978_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04066772

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