Dichloromethane → 3-(2,3-dihydro-5-methyl-2-oxo-1H-benzimidazol-1-yl)propyl methanesulfonate

HRID 258845Notes

Reaction equation

HRID 258845 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.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(N(CC)CC)C>[CH3:19][S:20]([O: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])(=[O:22])=[O:21]

Participants

5

Reactant 3

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

Product 1

HCID 214248263-(2,3-dihydro-5-methyl-2-oxo-1H-benzimidazol-1-yl)propyl methanesulfonateYield 58%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred solution 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 washed with water, dried, filtered and evaporated. The solid residue is crystallized from 4-methyl-2-pentanone, yielding 15 parts (58%) of 3-(2,3-dihydro-5-methyl-2-oxo-1H-benzimidazol-1-yl)propyl methanesulfonate; mp 125° C.

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. washthe reaction mixture is washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe solid residue is crystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-268333bb4d164576a19554028a95377e
Source dataset
uspto-grants-1977_07
Patent number
US04035369

Reaction notes

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