Methanesulfonyl chloride → 1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one methanesulfonate

HRID 46865Notes

Reaction equation

HRID 46865 reaction equation
[OH2:1].[OH:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:15].[CH3:16][S:17](Cl)(=[O:19])=[O:18]>N1C=CC=CC=1>[CH3:16][S:17]([OH:19])(=[O:1])=[O:18].[OH:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:15]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 203855841,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one hydrate

Product 1

HCID 867353601,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one methanesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 52.5 parts of 1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one hydrate in 200 parts of pyridine is added dropwise 63 parts of methanesulfonyl chloride. The mixture is stirred and cooled on the air for 2 hours. The pyridine is evaporated. To the residue is added 500 parts of water and the formed precipitate is filtered off. It is dissolved in 350 parts of trichloromethane. This solution is dried over magnesium sulfate and evaporated. The residue is crystallized from 40 parts of methylbenzene, yielding 25.5 parts of 1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one methanesulfonate; mp. 118°-120° C.

Workup

  1. temperaturecooled on the air for 2 hours
  2. customThe pyridine is evaporated
  3. additionTo the residue is added 500 parts of water
  4. filtrationthe formed precipitate is filtered off
  5. dissolutionIt is dissolved in 350 parts of trichloromethane
  6. dry with materialThis solution is dried over magnesium sulfate
  7. customevaporated
  8. customThe residue is crystallized from 40 parts of methylbenzene

Sources & evidence

ORD record
ord-c3276229829f43f3a1b20eeb3ae978b1
Source dataset
uspto-grants-1979_11
Patent number
US04175129

Reaction notes

Loading…