Triethylamine → HCID 19741630, compound

HRID 2255068Notes

Reaction equation

HRID 2255068 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.Cl.[Cl:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)=[CH:16][CH:15]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[ClH:12].[N:20]1([C:17]2[CH:18]=[CH:19][C:14]([CH2:13][N:9]([C:6]3[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=3)[NH2:10])=[CH:15][CH:16]=2)[CH:24]=[CH:23][N:22]=[CH:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 699814-Fluorophenylhydrazine hydrochloride2×HCID 197946621-[4-(chloromethyl)phenyl]-1H-imidazole hydrochloride

Product 1

HCID 19741630HCID 19741630, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 1-[4-1H-imidazol-1-yl)benzyl]-1-(4-fluorophenyl)hydrazine hydrochloride used above is prepared as follows: a mixture of 1-(4-fluorophenyl)hydrazine hydrochloride (3.3 g), 1-[4-(chloromethyl)phenyl]-1H-imidazole hydrochloride (3.1 g), triethylamine (6.6 ml) and toluene (200 ml) is refluxed under nitrogen for 13 hours. After cooling the mixture is filtered and the solution is evaporated to dryness. The residue is purified through a silica gel column eluiting with methylene chloride/methanol (100/5) to give 2.0 g of 1-[(4-1H-imidazol-1-yl)benzyl]-1-(4-fluorophenyl)hydrazine hydrochloride, ms: m/e 282 (M+), 158,157.

Workup

  1. customabove is prepared
  2. temperatureis refluxed under nitrogen for 13 hours
  3. temperatureAfter cooling the mixture
  4. filtrationis filtered
  5. customthe solution is evaporated to dryness
  6. customThe residue is purified through a silica gel column

Sources & evidence

ORD record
ord-b196b9df4c8146db9bce3370045ddb3a
Source dataset
uspto-grants-1993_08
Patent number
US05238953

Reaction notes

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