Sodium Hydroxide → HCID 14518708, compound

HRID 1723149Notes

Reaction equation

HRID 1723149 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)=[CH:4][C:3]=1[N+:14]([O-:16])=O.[N:17]1[CH:22]=[CH:21][C:20]([CH2:23][NH2:24])=[CH:19][CH:18]=1.[OH-].[Na+]>C(O)C>[N:9]1([CH2:8][C:5]2[CH:6]=[CH:7][C:2]3[N:24]=[C:23]([C:20]4[CH:21]=[CH:22][N:17]=[CH:18][CH:19]=4)[N:14]([OH:16])[C:3]=3[CH:4]=2)[CH:13]=[CH:12][N:11]=[CH:10]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 773174-PyridinemethanamineHCID 14990940HCID 14990940, compound

Product 1

HCID 14518708HCID 14518708, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 13.2 parts of 1-[(4-fluoro-3-nitrophenyl)methyl]-1H-imidazole, 13 parts of 4-pyridinemethanamine and 80 parts of ethanol was stirred for 6 hours at 60° C. 14.5 Parts of sodium hydroxide were added and the whole was stirred for 30 minutes at 60° C. The reaction mixture was evaporated. The residue was dissolved in 100 parts of water. Hydrochloric acid was added dropwise till a pH between 6 and 7 was reached. The product was filtered off, washed with water and 2-propanol and crystallized from 80 parts of 2-propanol. The product was filtered off and dried, yielding 10.7 parts (61%) of 6-(1H-imidazol-1-ylmethyl)-2-(4-pyridinyl)-1H-benzimidazol-1-ol; mp. 198.1° C. (compound 209).

Workup

  1. stirringthe whole was stirred for 30 minutes at 60° C
  2. customThe reaction mixture was evaporated
  3. dissolutionThe residue was dissolved in 100 parts of water
  4. additionHydrochloric acid was added dropwise till a pH between 6 and 7
  5. filtrationThe product was filtered off
  6. washwashed with water and 2-propanol
  7. customcrystallized from 80 parts of 2-propanol
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-254ba9a49f55421ea55122dd94f44b90
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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