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

HRID 1833626Notes

Reaction equation

HRID 1833626 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e933d1a697bc4accaf83ec2d65bccb52
Source dataset
uspto-grants-1978_01
Patent number
US04066772

Reaction notes

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