Tert-Butyl nitrite → HCID 15334497, compound

HRID 842137Notes

Reaction equation

HRID 842137 reaction equation
N[C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21][C:22]([F:25])([F:24])[F:23].N(OC(C)(C)C)=O>O1CCCC1>[C:19]([C:4]1[C:3]([S:21][C:22]([F:23])([F:25])[F:24])=[CH:2][N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:15])[F:16])=[CH:9][C:8]=2[Cl:18])[N:5]=1)#[N:20]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 9953940Fipronil sulfide

Product 1

HCID 15334497HCID 15334497, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole (4.0 g) in dry tetrahydrofuran (20 ml) was treated with tert-butyl nitrite (5.76 g) at room temperature. The mixture was then heated under reflux for 3 hours and evaporated in vacuo to give a yellow solid. Purification by chromatography eluting with petroleum ether/dichloromethane (2:1) gave 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole (3.12 g), m.p. 126.5-128° C., in the form of a white solid. By proceeding in a similar manner but replacing the 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole by the following phenylpyrazoles, there was obtained:

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 3 hours
  3. customevaporated in vacuo
  4. customto give a yellow solid
  5. customPurification by chromatography
  6. washeluting with petroleum ether/dichloromethane (2:1)

Sources & evidence

ORD record
ord-6e912ccfb6fe4939839a3d5835bbdca8
Source dataset
uspto-grants-2002_04
Patent number
US06372774B1

Reaction notes

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