4-benzenesulphonyl-5-methylsulphanyl-2H-pyrazol-3-ylamine → 8-benzenesulphonyl-2-methyl-7-methylsulphanyl-3H-pyrazolo[1,5-a][1,3,5]-triazin-4-one

HRID 636458Notes

Reaction equation

HRID 636458 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([S:7][CH3:8])[C:3]=1[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10].C(O[C:21](=[N:23][C:24](=O)[O:25]CC)[CH3:22])C>C(O)(=O)C>[C:12]1([S:9]([C:3]2[C:4]([S:7][CH3:8])=[N:5][N:6]3[C:24](=[O:25])[NH:23][C:21]([CH3:22])=[N:1][C:2]=23)(=[O:11])=[O:10])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 110547174-benzenesulphonyl-5-methylsulphanyl-2H-pyrazol-3-ylamineHCID 54019727Ethyl N-(ethoxycarbonyl)ethanimidate

Product 1

HCID 1355493298-benzenesulphonyl-2-methyl-7-methylsulphanyl-3H-pyrazolo[1,5-a][1,3,5]-triazin-4-oneYield 61%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 0.54 g (2 mol) of 5-amino-3-methylthio-4-phenylsulphonyl-pyrazole and 0.54 g (3.4 mmol) of ethyl 1-ethoxy-ethylidene-carbamate in acetic acid was stirred at 100° C. for 3 hrs. After cooling to RT the precipitate was filtered off, washed off with a copious amount of Et2O and dried in a high vacuum at 45° C. There was obtained 0.41 g (61%) of 8-benzenesulphonyl-2-methyl-7-methylsulphanyl-3H-pyrazolo[1,5-a][1,3,5]-triazin-4-one white crystals, m.p.>300° C.

Workup

  1. filtrationwas filtered off
  2. washwashed off with a copious amount of Et2O
  3. customdried in a high vacuum at 45° C

Sources & evidence

ORD record
ord-92475012f6bf4b3d96f83e105490f305
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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