Hydrochloric Acid → 2-amino-1-((4-fluorophenyl)methyl)-1H-benzimidazole

HRID 704713Notes

Reaction equation

HRID 704713 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[C:11]([NH2:16])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][CH:3]=1.Cl.[N:18]#[C:19]N.[OH-].[Na+]>O.CN(C)C=O.ClC(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:16]=[C:19]2[NH2:18])=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 14798Sodium HydroxideHCID 114699771,2-Benzenediamine, N-[(4-fluorophenyl)methyl]-

Product 1

HCID 30193052-amino-1-((4-fluorophenyl)methyl)-1H-benzimidazoleYield 9.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred mixture of 23.5 parts of N-(4-fluorophenylmethyl)-1,2-benzenediamine and 14.4 parts of concentrated hydrochloric acid were added dropwise 9 parts of cyanamide at 100° C. After stirring for 3 hours at 100° C., there were added dropwise 10.5 parts of a sodium hydroxide solution 50%. Upon completion, stirring was continued overnight at reflux temperature. The reaction mixture was cooled and taken up in a mixture of water, trichloromethane and N,N-dimethylformamide. The organic phase was separated, dried, filtered and evaporated. The residue was stirred in trichloromethane. The product was filtered off and crystallized from trichloromethane, yielding 2.5 parts (9.5%) of 1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine; mp. 189.5° C. (int. 31).

Workup

  1. stirringUpon completion, stirring
  2. waitwas continued overnight
  3. temperatureat reflux temperature
  4. temperatureThe reaction mixture was cooled
  5. customThe organic phase was separated
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. stirringThe residue was stirred in trichloromethane
  10. filtrationThe product was filtered off
  11. customcrystallized from trichloromethane

Sources & evidence

ORD record
ord-ec2189935f5e431db1eb04aaa103b9f5
Source dataset
uspto-grants-1991_01
Patent number
US04988689

Reaction notes

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