Tert-Butyl nitrite → 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole

HRID 1274342Notes

Reaction equation

HRID 1274342 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[I:21].C(ON=O)(C)(C)C>O1CCCC1>[C:19]([C:4]1[C:3]([I:21])=[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 154620775-Amino-3-cyano-4-iodo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole

Product 1

HCID 211881263-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole (90 g) in tetrahydrofuran (720 ml) heated to 65° C. was added t-butylnitrite (144 ml) over a period of 0.5 hours. Stirring and heating were continued for 3 hours. The cooled reaction mixture was evaporated and the residue recrystallised from propan-2-ol to give the title compound as a white solid, m.p. 83-4° C.

Workup

  1. temperatureheating
  2. customThe cooled reaction mixture
  3. customwas evaporated
  4. customthe residue recrystallised from propan-2-ol

Sources & evidence

ORD record
ord-b06567815adc4499a6e4ef7d82ad8c5a
Source dataset
uspto-grants-2000_12
Patent number
US06156782

Reaction notes

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