Sodium borohydride → 2-{4-[4-(1-hydroxyethyl)benzyl]-3,5-dichlorophenyl}-4,5-dihydro-1,2,4-triazin-3(2H)-one

HRID 1604321Notes

Reaction equation

HRID 1604321 reaction equation
[C:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][C:9]2[C:14]([Cl:15])=[CH:13][C:12]([N:16]3[C:21](=[O:22])[NH:20][CH2:19][CH:18]=[N:17]3)=[CH:11][C:10]=2[Cl:23])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>C(O)C>[OH:3][CH:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][C:9]2[C:14]([Cl:15])=[CH:13][C:12]([N:16]3[C:21](=[O:22])[NH:20][CH2:19][CH:18]=[N:17]3)=[CH:11][C:10]=2[Cl:23])=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 220085612-[4-(4-acetylbenzyl)-3,5-dichlorophenyl]-4,5-dihydro-1,2,4-triazin-3(2H)-one

Product 1

HCID 220085602-{4-[4-(1-hydroxyethyl)benzyl]-3,5-dichlorophenyl}-4,5-dihydro-1,2,4-triazin-3(2H)-oneYield 86.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 1.5 ml of ethanol was suspended 0.15 g of 2-[4-(4-acetylbenzyl)-3,5-dichlorophenyl]-4,5-dihydro-1,2,4-triazin-3(2H)-one. To the suspension was added 0.1 g of sodium borohydride. The mixture was stirred for one hour at room temperature. The reaction mixture was poured into 10 ml ice-water, followed by extraction with 10 ml of ethylacetate. The extract was dried over anhydrous magnesium sulfate, and concentrated. This residue was purified by column chromatography (Merck Silica Gel 60; hexane-acetone=1:1) to provide 0.13 g of the title compound as colorless crystals, m.p. 119-120° C.

Workup

  1. extractionfollowed by extraction with 10 ml of ethylacetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThis residue was purified by column chromatography (Merck Silica Gel 60; hexane-acetone=1:1)

Sources & evidence

ORD record
ord-faa2660d8c0d4accad558238a41f9cfa
Source dataset
uspto-grants-1999_11
Patent number
US05994355

Reaction notes

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