Tert-Butyl nitrite → HCID 18929395, compound

HRID 1598518Notes

Reaction equation

HRID 1598518 reaction equation
CS[S:3][CH3:4].N(OC(C)(C)C)=O.N[C:13]1[N:17]([CH3:18])[N:16]=[C:15]([C:19]2[C:24]([Cl:25])=[CH:23][C:22]([C:26]([F:29])([F:28])[F:27])=[CH:21][C:20]=2[Cl:30])[C:14]=1[N+:31]([O-:33])=[O:32]>C(Cl)Cl>[Cl:25][C:24]1[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=[C:20]([Cl:30])[C:19]=1[C:15]1[C:14]([N+:31]([O-:33])=[O:32])=[C:13]([S:3][CH3:4])[N:17]([CH3:18])[N:16]=1

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 12232Dimethyl DisulfideHCID 18929413HCID 18929413, compound

Product 1

HCID 18929395HCID 18929395, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

First 1.4 g of dimethyl disulfide and then 0.96 g of tert-butyl nitrite were added at 0° C. to a solution of 1.1 g of 5-amino-3-(2,6-dichloro-4-trifluoromethylphenyl)-1-methyl-4-nitropyrazole (14) in 25 ml of anhydrous methylene chloride, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, the resulting residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/1) to afford 0.6 g of the desired compound in the form of a yellow consistent liquid (yield 60.1%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-ffc82e7f0c3f4cffa3e45125ad8cf354
Source dataset
uspto-grants-1998_04
Patent number
US05739083

Reaction notes

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