3-ethyl-1H-pyrazol-5-amine → 4-(2,4-Dichlorophenyl)-7-ethyl-2-methyl-pyrazolo[1,5-a]-1,3,5-triazine

HRID 1794994Notes

Reaction equation

HRID 1794994 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([CH2:7][CH3:8])[NH:4][N:3]=1.CS[C:11](=[N:13][C:14](=O)[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])[CH3:12]>O1CCOCC1>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[C:14]1[N:3]2[N:4]=[C:5]([CH2:7][CH3:8])[CH:6]=[C:2]2[N:1]=[C:11]([CH3:12])[N:13]=1

Participants

4

Reactant 2

HCID 219910953-ethyl-1H-pyrazol-5-amineHCID 22184679N-(1-(methylthio)ethylidene)-2,4-dichlorobenzamide

Product 1

HCID 221846894-(2,4-Dichlorophenyl)-7-ethyl-2-methyl-pyrazolo[1,5-a]-1,3,5-triazineYield 14%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-amino-5-ethylpyrazole (10.3 g, 39.3 mmol) and N-(1-(methylthio)ethylidene)-2,4-dichloro-benzamide (4.0 g, 35.7 mmol) in anhydrous dioxan (20 mL) was stirred at reflux temperature under a nitrogen atmosphere for 16 h. After being cooled to ambient temperature, the reaction mix was concentrated in vacuo and the residue was treated with dichloromethane. The resulting suspension was filtered and the filtrate was concentrated in vacuo to afford an oil (1.5 g, 14% yield): NMR (CDCl3, 300 MHz): δ 7.62 (d, 1H, J=8), 7.59 (d, 1H, J=2), 7.45 (dd, 1H, J=8,2), 6.42 (s, 1H), 2.82 (q, 2H, J=8), 2.73 (s, 3H), 1.30 (t, 3H, J=8).

Workup

  1. temperatureat reflux temperature under a nitrogen atmosphere for 16 h
  2. additionthe reaction mix
  3. concentrationwas concentrated in vacuo
  4. additionthe residue was treated with dichloromethane
  5. filtrationThe resulting suspension was filtered
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-60f5b91a3e354182ad453b3c35661653
Source dataset
uspto-grants-2006_04
Patent number
US07026317B2

Reaction notes

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