Benzene → 6-[4-(2-furylmethylenamino)phenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

HRID 2290268Notes

Reaction equation

HRID 2290268 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.[CH:16](=O)[C:17]1[O:21][CH:20]=[CH:19][CH:18]=1.CN(C=O)C.C1C=CC=CC=1>O>[O:21]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH:16]=[N: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

Participants

6

Reactant 4

HCID 241BenzeneHCID 6228DimethylformamideHCID 7362FurfuralHCID 133860336-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

Product 1

HCID 202321506-[4-(2-furylmethylenamino)phenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-oneYield 89.3%

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 (2 g), furfural (1.41 g), DMF (25 ml) and benzene (25 ml) was refluxed in an apparatus equipped with a Dean-Stark water separator for 3 hours. The reaction mixture was evaporated in vacuo and the resultant residue was triturated with diethyl ether to give 6-[4-(2-furylmethylenamino)phenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (2.47 g).

Workup

  1. temperaturewas refluxed in an apparatus
  2. customThe reaction mixture was evaporated in vacuo
  3. customthe resultant residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-ea02c8cf49e44528a64cd5560adbf37c
Source dataset
uspto-grants-1986_10
Patent number
US04616015

Reaction notes

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