Thionyl Chloride → 1-(2-chloroethyl)-1,3-dihydro-5-methyl-2H-benzimidazol-2-one

HRID 258834Notes

Reaction equation

HRID 258834 reaction equation
O[CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([CH3:13])=[CH:12][C:7]=2[NH:6][C:5]1=[O:14].S(Cl)([Cl:17])=O>ClC(Cl)Cl>[Cl:17][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([CH3:13])=[CH:12][C:7]=2[NH:6][C:5]1=[O:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 214248171-(2-Hydroxyethyl)-5-methyl-1H-benzo[d]imidazol-2(3H)-one

Product 1

HCID 214248251-(2-chloroethyl)-1,3-dihydro-5-methyl-2H-benzimidazol-2-oneYield 42%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 26 parts of 1,3-dihydro-1-(2-hydroxyethyl)-5-methyl-2H-benzimidazol-2-one and 390 parts of trichloromethane are added dropwise 48 parts of sulfinyl chloride at room temperature. Upon completion, stirring is continued for 5 hours at reflux. The reaction mixture is evaporated. The oily residue is heated with 2,2'-oxybispropane and a small amount of 2-propanol and the whole is stirred with activated charcoal. The latter is filtered off and the filtrate is stirred at room temperature till all the product is precipitated. It is filtered off and dried, yielding 12 parts (42%) of 1-(2-chloroethyl)-1,3-dihydro-5-methyl-2H-benzimidazol-2-one; mp. 120° C.

Workup

  1. temperatureat reflux
  2. customThe reaction mixture is evaporated
  3. temperatureThe oily residue is heated with 2,2'-oxybispropane
  4. stirringa small amount of 2-propanol and the whole is stirred with activated charcoal
  5. filtrationThe latter is filtered off
  6. stirringthe filtrate is stirred at room temperature till all the product
  7. customis precipitated
  8. filtrationIt is filtered off
  9. customdried

Sources & evidence

ORD record
ord-ae3e2045c00c42aa84b57550a4e4f0b0
Source dataset
uspto-grants-1977_07
Patent number
US04035369

Reaction notes

Loading…