Dichloromethane → 1,3-dihydro-1-(3-hydroxypropyl)-5-methyl-2H-benzimidazol-2-one methanesulfonate

HRID 2420291Notes

Reaction equation

HRID 2420291 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=2[NH:7][C:6]1=[O:15].ClCCl.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>O>[CH3:26][S:27]([OH:29])(=[O:1])=[O:28].[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=2[NH:7][C:6]1=[O:15]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 203855821,3-dihydro-1-(3-hydroxypropyl)-5-methyl-2H-benzimidazol-2-one

Product 1

HCID 867353561,3-dihydro-1-(3-hydroxypropyl)-5-methyl-2H-benzimidazol-2-one methanesulfonateYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solutions of 18.5 parts of 1,3-dihydro-1-(3-hydroxypropyl)-5-methyl-2H-benzimidazol-2-one in 325 parts of dichloromethane are added 11.9 parts of N,N-diethylethanamine. Then there are added dropwise (slowly) 11.5 parts of methanesulfonyl chloride. Upon completion, stirring is continued for 1 hour at reflux temperature. After cooling, the reaction mixture is washeed with water, dried, filtered and evaporated. The solid residue is crystallized from 4-methyl-2-pentanone, yielding 15 parts (58%) of 1,3-dihydro-1-(3-hydroxypropyl)-5-methyl-2H-benzimidazol-2-one methanesulfonate; mp. 125° C.

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe solid residue is crystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-e95be8328e504bab8100207615cba2eb
Source dataset
uspto-grants-1978_08
Patent number
US04110333

Reaction notes

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