Toluene → HCID 19754619, compound

HRID 1588802Notes

Reaction equation

HRID 1588802 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17](N)=[C:16]([S:19][C:20]([F:23])([F:22])[F:21])[N:15]=[CH:14]1.C(Br)(Br)[Br:25].C(ON=O)(C)(C)C.C1(C)C=CC=CC=1>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([Br:25])=[C:16]([S:19][C:20]([F:23])([F:22])[F:21])[N:15]=[CH:14]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 5558BromoformHCID 10906Tert-Butyl nitriteHCID 19754602HCID 19754602, compound

Product 1

HCID 19754619HCID 19754619, compoundYield 34.44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2.0 g (5.05 mmole) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-amino-4-trifluoromethylsulfenylimidazole in 10 ml of acetonitrile was added 1 ml of bromoform and 1.20 ml (10.10 mmole) of t-butylnitrite at 0° C. The resulting mixture was stirred at RT under a nitrogen atmosphere for 1.5 h. Ten ml of toluene was added and the mixture was evaporated to dryness under vacuum. The residue was purified by column chromatography on silica gel using 5% ethyl acetate in hexane to give 800 mg (34.44% yield) of the desired product, mp 87.5° C.

Workup

  1. customthe mixture was evaporated to dryness under vacuum
  2. customThe residue was purified by column chromatography on silica gel using 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3cdbeaeca9464325bdb73782f00772c7
Source dataset
uspto-grants-1993_06
Patent number
US05223525

Reaction notes

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