Hydrochloric Acid → 1,3-dihydro-1-(3-hydroxypropyl)-5-methyl-2H-benzimidazol-2-one

HRID 1833617Notes

Reaction equation

HRID 1833617 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][OH:13].Cl.[O-:15][C:16]#N.[K+]>O>[OH:13][CH2:12][CH2:11][CH2:10][N:9]1[C:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[NH:1][C:16]1=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11378442Potassium cyanateHCID 203856153-[(2-Amino-4-methylphenyl)amino]-1-propanol

Product 1

HCID 203855821,3-dihydro-1-(3-hydroxypropyl)-5-methyl-2H-benzimidazol-2-oneYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred and cooled solution of 54 parts of 3-[(2-amino-4-methylphenyl)amino]-1-propanol in 30 parts of hydrochloric acid solution 10% and 200 parts of water is added dropwise a solution of 28 parts of potassium cyanate in 50 parts of water at a temperature below 10° C. Upon completion, stirring is continued first for 1 hour at room temperature and further for 24 hours at reflux temperature. After cooling to room temperature, the product is extracted with trichloromethane. The extract is washed with a hydrochloric acid solution 5%, dried, filtered and evaporated. The residue is crystallized from 4-methyl-2-pentanone, yielding 19.5 parts (31%) of 1,3-dihydro-1-(3-hydroxypropyl)-5-methyl-2H-benzimidazol-2-one; mp. 114.1° C.

Workup

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

Sources & evidence

ORD record
ord-9e4b4b1e64ac4e6bbd7a74c7475b4597
Source dataset
uspto-grants-1978_01
Patent number
US04066772

Reaction notes

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