5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile → HCID 17856314, compound

HRID 470654Notes

Reaction equation

HRID 470654 reaction equation
N[C:2]1[N:6](C2C(Cl)=CC(C(F)(F)F)=CC=2Cl)[N:5]=[C:4](C#N)[CH:3]=1.[F:21][C:22]([F:33])([F:32])[S:23]([N:25]1C(=O)CCC1=O)=[O:24]>C(N(CC)CC)C>[F:21][C:22]([F:33])([F:32])[S:23]([NH:25][N:6]1[CH:2]=[CH:3][CH:4]=[N:5]1)=[O:24]

Participants

4

Reactant 2

HCID 33039135-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrileHCID 10214488HCID 10214488, compound

Product 1

HCID 17856314HCID 17856314, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

As described in EP-A 1 331 222, 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile (II) is sulfinylated using N-trifluoromethylsulfinylsuccinimide as the sulfinylating agent in the presence of triethylamine and without the addition of a chlorinating agent. The intermediate N-trifluoromethylsulfinylamino-pyrazole is isolated and under the conditions of a Thia-Fries rearrangement transformed into the final product 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)-pyrazole-3-carbonitrile.

Workup

  1. additionwithout the addition of a chlorinating agent

Sources & evidence

ORD record
ord-db14dccb6fd24542ba264169d1874c5f
Source dataset
uspto-grants-2014_01
Patent number
US08629287B2

Reaction notes

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