Water → HCID 20379499, compound

HRID 2051683Notes

Reaction equation

HRID 2051683 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH2:18])[C:6]([NH:9][CH:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH3:11])=[CH:7][CH:8]=1.N[C:20](N)=[O:21].O>ClC(Cl)Cl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]2[N:9]([CH:10]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[CH3:11])[C:20](=[O:21])[NH:18][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1176UreaHCID 70611928HCID 70611928, compound

Product 1

HCID 20379499HCID 20379499, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 41.5 parts of 4-chloro-N1 -[1-(3-pyridinyl)ethyl]-1,2-benzenediamine monohydrochloride and 27 parts of urea is stirred and heated for 1.50 hours in an oil-bath at about 190° C. The reaction mixture is cooled, water and trichloromethane are added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane. The product is filtered off and dried, yielding 26 parts (63.5%) of 5-chloro-1,3-dihydro-1-[1-(3-pyridinyl)ethyl]-2H-benzimidazol-2-one; mp. 190° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe layers are separated
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane
  7. filtrationThe product is filtered off
  8. customdried

Sources & evidence

ORD record
ord-cd21ca143bca4a98bcb583afcd719697
Source dataset
uspto-grants-1980_01
Patent number
US04181802

Reaction notes

Loading…