N,N-Dimethylaniline → 6-[4-(2-acetoxypropionylamino)phenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

HRID 2290279Notes

Reaction equation

HRID 2290279 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.CN(C)C1C=CC=CC=1.[C:25]([O:28][CH:29]([CH3:33])[C:30](Cl)=[O:31])(=[O:27])[CH3:26]>CN(C=O)C>[C:25]([O:28][CH:29]([CH3:33])[C:30]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:6][CH:7]=1)=[O:31])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 45474922-Acetoxypropionyl ChlorideHCID 133860336-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

Product 1

HCID 202321356-[4-(2-acetoxypropionylamino)phenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-oneYield 72.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (1.0 g) and N,N-dimethylaniline (0.93 ml) in DMF (10 ml) was added dropwise 2-acetoxypropionyl chloride (0.98 g) under ice cooling. The stirring was continued for one night at ambient temperature. The mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate after addition of saline solution. The extract was washed successively with 1N hydrochloric acid, water and saline solution, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (170 ml) with a mixture of chloroform and methanol (10:1) as an eluent. The eluates containing the object compound were evaporated in vacuo to give 1.13 g of 6-[4-(2-acetoxypropionylamino)phenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one.

Workup

  1. waitThe stirring was continued for one night at ambient temperature
  2. concentrationThe mixture was concentrated under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate
  4. additionafter addition of saline solution
  5. washThe extract was washed successively with 1N hydrochloric acid, water and saline solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was chromatographed on silica gel (170 ml) with a mixture of chloroform and methanol (10:1) as an eluent
  9. additionThe eluates containing the object compound
  10. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-cd1539bb69df4a4bade3889cd256d39c
Source dataset
uspto-grants-1986_10
Patent number
US04616015

Reaction notes

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