Hydrochloric Acid → HCID 22161905, compound

HRID 1088732Notes

Reaction equation

HRID 1088732 reaction equation
[C:1]([C:3]1[C:7]([S:8]([C:11]([F:14])([F:13])[F:12])(=[O:10])=[O:9])=[C:6]([NH:15][NH2:16])[N:5]([C:17]2[C:22]([Cl:23])=[CH:21][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][C:18]=2[Cl:28])[N:4]=1)#[N:2].CO[CH:31](OC)[CH2:32][CH:33](OC)OC.Cl>C(O)C>[C:1]([C:3]1[C:7]([S:8]([C:11]([F:12])([F:13])[F:14])(=[O:10])=[O:9])=[C:6]([N:15]2[CH:33]=[CH:32][CH:31]=[N:16]2)[N:5]([C:17]2[C:22]([Cl:23])=[CH:21][C:20]([C:24]([F:26])([F:25])[F:27])=[CH:19][C:18]=2[Cl:28])[N:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66019TetramethoxypropaneHCID 22161910HCID 22161910, compound

Product 1

HCID 22161905HCID 22161905, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-hydrazino-4-trifluoromethylsulphonylpyrazole (1.6 g), 1,1,3,3-tetramethoxypropane (0.58 g), ethanol (10 ml) and concentrated hydrochloric acid (1 ml) was heated under reflux for 4 hours. After evaporation in vacuo the residue was dissolved in dichloromethane (200 ml) and washed in turn with sodium bicarbonate solution (2×50 ml) and with water (50 ml). Filtration (phase separating paper), followed by evaporation gave a red solid, which was purified by chromatography on silica, eluting with dichloromethane/hexane (1:1). The product was recrystallised from toluene giving 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-pyrazol-1-yl-4-trifluoromethylsulphonylpyrazole (0.6 g) as a white solid, m.p. 191°-193° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. customAfter evaporation in vacuo the residue
  4. dissolutionwas dissolved in dichloromethane (200 ml)
  5. washwashed in turn with sodium bicarbonate solution (2×50 ml) and with water (50 ml)
  6. filtrationFiltration (phase separating paper)
  7. customfollowed by evaporation
  8. customgave a red solid, which
  9. customwas purified by chromatography on silica
  10. washeluting with dichloromethane/hexane (1:1)
  11. customThe product was recrystallised from toluene

Sources & evidence

ORD record
ord-2961e95c00fe43e184ac0ea575d73d99
Source dataset
uspto-grants-1990_10
Patent number
US04963575

Reaction notes

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