Dimethylformamide → 6-(4-amino-3-chlorophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

HRID 2290739Notes

Reaction equation

HRID 2290739 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.[Cl:16]N1C(=O)CCC1=O.CN(C)C=O>O>[NH2:1][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][C:7]=1[Cl:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 133860336-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

Product 1

HCID 133860536-(4-amino-3-chlorophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-oneYield 8.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (0.2 g), N-chlorosuccinimide (0.135 g) and dimethylformamide (3 ml) was stirred with ice-cooling for an hour. The reaction mixture was poured into water and extracted with chloroform. The extract was concentrated to dryness under reduced pressure and the residue was crystallized from chloroform to give 6-(4-amino-3-chlorophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (0.02 g).

Workup

  1. temperaturecooling for an hour
  2. extractionextracted with chloroform
  3. concentrationThe extract was concentrated to dryness under reduced pressure
  4. customthe residue was crystallized from chloroform

Sources & evidence

ORD record
ord-e50ab9fd73bd4f99acf4bd6794c3c83f
Source dataset
uspto-grants-1986_10
Patent number
US04618610

Reaction notes

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