Hydrochloric Acid → HCID 53978413, compound

HRID 1650798Notes

Reaction equation

HRID 1650798 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH2:26][N:27]1[CH:31]=[N:30][CH:29]=[N:28]1)([OH:25])[CH2:10][N:11]1[CH:15]=[N:14][C:13]([CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=[N:12]1.[H-].[Na+].[H][H].[Cl:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41]Cl)=[CH:39][CH:38]=1.Cl>CN1CCCC1=O>[Cl:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][O:24][C:21]2[CH:22]=[CH:23][C:18]([CH:17]=[CH:16][C:13]3[N:14]=[CH:15][N:11]([CH2:10][C:9]([C:3]4[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=4[F:1])([CH2:26][N:27]4[CH:31]=[N:30][CH:29]=[N:28]4)[OH:25])[N:12]=3)=[CH:19][CH:20]=2)=[CH:39][CH:38]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 135970796HCID 135970796, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53978413HCID 53978413, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1-(2,4-Difluorophenyl)-2-[3-(4-hydroxystyryl)-1,2,4-triazol-1-yl]-1-(1,2,4-triazol-1-ylmethyl)ethanol (710 mg) was dissolved in N-methylpyrrolidone (10 ml., dried over molecular sieve), and sodium hydride (57% dispersion in oil, 75 mg) was added in portions. When the evolution of hydrogen had ceased, p-chlorobenzyl chloride (300 mg) was added, and the mixture was stirred at 80° for 3 hours and then for 18 hours at room temperature. The reaction mixture was poured into 0.1N hydrochloric acid and extracted with ethyl acetate. The extracts were combined, washed successively with water, 0.5N sodium hydroxide solution (twice), water and brine, and was then filtered through anhydrous sodium sulphate. The filtrate was evaporated, and the crude product was purified by medium pressure liquid chromatography, eluting with chloroform, to give 2-[3-(4-p-chlorobenzyloxystyryl)-1,2,4-triazol-1-yl]-1-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-ylmethyl)ethanol, crystallised from diethylether/ethyl acetate/petroleum ether, m.p. 103°-106°.

Workup

  1. waitfor 18 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed successively with water, 0.5N sodium hydroxide solution (twice), water and brine
  4. filtrationwas then filtered through anhydrous sodium sulphate
  5. customThe filtrate was evaporated
  6. customthe crude product was purified by medium pressure liquid chromatography
  7. washeluting with chloroform

Sources & evidence

ORD record
ord-37531e30c1ca40098011b9939c22616e
Source dataset
uspto-grants-1990_05
Patent number
US04925863

Reaction notes

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