p-Toluenesulfonic acid → HCID 54046983, compound

HRID 1090597Notes

Reaction equation

HRID 1090597 reaction equation
[NH2:1][N:2]1[C:6]([NH:7][CH3:8])=[N:5][NH:4][C:3]1=[O:9].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:21](OCC)(OCC)[O:22][CH2:23][CH3:24]>>[CH2:23]([O:22][CH:21]=[N:1][N:2]1[C:6]([NH:7][CH3:8])=[N:5][NH:4][C:3]1=[O:9])[CH3:24]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 15116961HCID 15116961, compound

Product 1

HCID 54046983HCID 54046983, compoundYield 54%

Procedure

12.9 g (0.1 mol) of 4-amino-5-methylamino-2,4-dihydro-3H-1,2,4-triazol-3-one are refluxed for 4 hours with 100 ml of triethyl orthoformate and 100 mg of p-toluenesulphonic acid. The mixture is then concentrated and crystallized with diethyl ether. Recrystallization from ethanol gives 10.0 g (54% of theory) of 4-ethoxymethyleneamino-5-methylamino-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 169° C.

Workup

  1. concentrationThe mixture is then concentrated
  2. customcrystallized with diethyl ether
  3. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-3cb1e683933c45d9add5b8da6a359009
Source dataset
uspto-grants-1992_01
Patent number
US05082490

Reaction notes

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