Hydrochloric Acid → HCID 53980427, compound

HRID 976318Notes

Reaction equation

HRID 976318 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)[C:9]2[CH:14]=[CH:13][C:12]([NH:15]C(=O)C)=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)[C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19967116HCID 19967116, compound

Product 1

HCID 53980427HCID 53980427, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 80 parts of intermediate 47, namely N-[4-[(3-chlorophenyl) (1H-imidazol-1-yl)methyl]phenyl]acetamide, 150 ml of an aqueous hydrochloric acid solution 2N and 15.8 parts of methanol was stirred for 2 hours at reflux temperature. The reaction mixture was evaporated and the residue was basified. The product was extracted with dichloromethane and the extract was dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 98:2). The eluent of the desired fraction was evaporated, yielding 14.1 parts (20.2%) of 4-[(3-chlorophenyl) (1H-imidazol-1-yl)methyl]benzenamine (interm. 48).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. extractionThe product was extracted with dichloromethane
  4. customthe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 98:2)
  8. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-d26646f4888a4169ad37235c937c86c6
Source dataset
uspto-grants-1997_03
Patent number
US05612354

Reaction notes

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