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

HRID 1704529Notes

Reaction equation

HRID 1704529 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][CH2:13][CH2:14][CH2:15][OH:16].Cl.[O-:18][C:19]#N.[K+]>O>[OH:16][CH2:15][CH2:14][CH2:13][N:12]1[C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:7][C:2]=2[NH:1][C:19]1=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11378442Potassium cyanateHCID 203855523-{[2-Amino-4-(trifluoromethyl)phenyl]amino}-1-propanol

Product 1

HCID 203856341,3-dihydro-1-(3-hydroxypropyl)-5-(trifluoromethyl)-2H-benzimidazol-2-oneYield 34%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred mixture of 21 parts of 3-{[2-amino-4-(trifluoromethyl)phenyl]amino}-1-propanol and 100 parts of water are added 14.4 parts of hydrochloric acid solution. The whole is stirred for 10 minutes at room temperature. After cooling to 0°-10° C., there is added dropwise a solution of 18 parts of potassium cyanate in 50 parts of water. Upon completion, stirring is continued for 2 hours. The precipitated product is filtered off and dried. Then it is melted and the melt is stirred for 10 minutes. After cooling, it is dissolved in trichloromethane while heating. The solution is filtered and the product is allowed to crystallize from the filtrate. It is filtered off and dried, yielding 8 parts (34%) of 1,3-dihydro-1-(3-hydroxypropyl)-5-(trifluoromethyl)-2H-benzimidazol-2-one.

Workup

  1. temperatureAfter cooling to 0°-10° C.
  2. stirringUpon completion, stirring
  3. waitis continued for 2 hours
  4. filtrationThe precipitated product is filtered off
  5. customdried
  6. stirringthe melt is stirred for 10 minutes
  7. temperatureAfter cooling
  8. dissolutionit is dissolved in trichloromethane
  9. temperaturewhile heating
  10. filtrationThe solution is filtered
  11. customto crystallize from the filtrate
  12. filtrationIt is filtered off
  13. customdried

Sources & evidence

ORD record
ord-326a0b2c6ef44ab294b0ac623b03e205
Source dataset
uspto-grants-1978_11
Patent number
US04126688

Reaction notes

Loading…