Sodium hydride → HCID 13469432, compound

HRID 2290277Notes

Reaction equation

HRID 2290277 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]([CH3:21])[NH:16][C:17](=[O:20])[NH:18][N:19]=2)=[CH:10][CH:9]=1)=[O:6].[H-].[Na+]>CN(C=O)C>[O:6]=[C:5]1[CH2:4][CH2:3][CH2:2][N:7]1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]([CH3:21])[NH:16][C:17](=[O:20])[NH:18][N:19]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 20232138HCID 20232138, compound

Product 1

HCID 13469432HCID 13469432, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 6-[4-(4-chlorobutyrylamino)phenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (3.879 g) in DMF (38 ml) was added dropwise to a stirred mixture of sodium hydride (1.055 g) in DMF (13 ml) under ice cooling and stirring was continued for 30 minutes. The mixture was evaporated in vacuo after addition of acetic acid (1.85 ml) thereto. Water was added to the residue and the resultant precipitates were collected by filtration and recrystallized 70% aqueous ethanol to give 6-[4-(2oxo-1-pyrrolidinyl)phenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (1.77 g).

Workup

  1. customThe mixture was evaporated in vacuo
  2. additionafter addition of acetic acid (1.85 ml)
  3. additionWater was added to the residue
  4. customthe resultant precipitates
  5. filtrationwere collected by filtration
  6. customrecrystallized 70% aqueous ethanol

Sources & evidence

ORD record
ord-f84f166502864a3bb90b7a701adfc89b
Source dataset
uspto-grants-1986_10
Patent number
US04616015

Reaction notes

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