Triethylamine → 5-chloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one methanesulfonate

HRID 971739노트

반응식

HRID 971739 반응식
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:10][CH2:11][CH2:12][OH:13])[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH3:23][S:24]([OH:26])(=[O:9])=[O:25].[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:10][CH2:11][CH2:12][OH:13])[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 30173585-chloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one

생성물 1

HCID 867353595-chloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one methanesulfonate수율 53%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred and cooled (ice-water bath) mixture of 14.1 parts of 5-chloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one, 8 parts of N,N-diethylethanamine and 195 parts of dichloromethane are added dropwise 7.8 parts of methanesulfonyl chloride. Upon completion, stirring is continued first for 15 minutes while still cooling an further for 1 hour at reflux temperature. The dichloromethane is evaporated and the residue is dissolved in 4-methyl-2-pentanone and water while heating. The layers are separated and the organic phase is stirred with 100 parts of water, while cooling in an ice-bath. The precipitated product is filtered off and dried, yielding 10 parts (53%) of 5-chloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one methanesulfonate; mp. 140° C.

후처리

  1. temperaturecooled
  2. stirringUpon completion, stirring
  3. temperaturewhile still cooling an further for 1 hour
  4. temperatureat reflux temperature
  5. customThe dichloromethane is evaporated
  6. dissolutionthe residue is dissolved in 4-methyl-2-pentanone
  7. temperaturewater while heating
  8. customThe layers are separated
  9. stirringthe organic phase is stirred with 100 parts of water
  10. temperaturewhile cooling in an ice-bath
  11. filtrationThe precipitated product is filtered off
  12. customdried

출처 및 근거

ORD 기록
ord-3147bbec8b5041ac8aeadd298b5c2740
출처 데이터셋
uspto-grants-1979_07
특허 번호
US04160836

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