Hydrochloric Acid → 4-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-one

HRID 46855Notes

Reaction equation

HRID 46855 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][OH:13].Cl.[O-:15][C:16]#N.[K+]>O>[Cl:8][C:4]1[C:3]2[N:9]([CH2:10][CH2:11][CH2:12][OH:13])[C:16](=[O:15])[NH:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11378442Potassium cyanateHCID 203856203-[(2-Amino-6-chlorophenyl)amino]-1-propanol

Product 1

HCID 203855604-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-oneYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred and cooled (10° C.) mixture of 20 parts of 3-[(2-amino-6-chlorophenyl)amino]-1-propanol, 12 parts of a hydrochloric acid solution and 100 parts of water is added dropwise a solution of 9 parts of potassium cyanate in 30 parts of water. Upon completion, stirring is continued first for 2 hours at room temperature and further overnight at reflux temperature. After cooling, the product is extracted with trichloromethane. The extract is washed with a diluted hydrochloric acid solution, dried, filtered and evaporated. The residue is crystallized from 4-methyl-2-pentanone, yielding 9 parts (41%) of 4-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-one.

Workup

  1. temperaturecooled
  2. stirringUpon completion, stirring
  3. temperatureat reflux temperature
  4. temperatureAfter cooling
  5. extractionthe product is extracted with trichloromethane
  6. washThe extract is washed with a diluted hydrochloric acid solution
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is crystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-3a77e67138c24992bb48b4aa847269b5
Source dataset
uspto-grants-1979_11
Patent number
US04175129

Reaction notes

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