Triethylamine → 4-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-one methanesulfonate

HRID 1833626ノート

反応式

HRID 1833626 の反応式
[Cl:1][C:2]1[C:10]2[N:9]([CH2:11][CH2:12][CH2:13][OH:14])[C:8](=[O:15])[NH:7][C:6]=2[CH:5]=[CH:4][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:14])=[O:25].[Cl:1][C:2]1[C:10]2[N:9]([CH2:11][CH2:12][CH2:13][OH:14])[C:8](=[O:15])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 203855604-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-one

生成物 1

HCID 867353584-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-one methanesulfonate収率 75%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred mixture of 9 parts of 4-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-one, 7 parts of N,N-diethylethanamine and 130 parts of dichloromethane are added dropwise 12 parts of methanesulfonyl chloride (exothermic reaction: temperature rises to reflux). Upon completion, stirring is continued for 1 hour at reflux temperature. The reaction mixture is cooled and poured onto water. The organic phase is separated, washed with acidified water, dried, filtered and evaporated. The residue is crystallized from 4-methyl-2-pentanone, yielding 9 parts (75%) of 4-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-one methanesulfonate.

後処理

  1. temperatureat reflux temperature
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water
  4. customThe organic phase is separated
  5. washwashed with acidified water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is crystallized from 4-methyl-2-pentanone

出典と根拠

ORDレコード
ord-e933d1a697bc4accaf83ec2d65bccb52
出典データセット
uspto-grants-1978_01
特許番号
US04066772

反応ノート

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