Tert-Butyl nitrite → HCID 19754616, compound

HRID 1588800Notes

Reaction equation

HRID 1588800 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]=[C:14]1[Cl:24].[CH3:25][S:26]SC.C(ON=O)(C)(C)C>C(Cl)(Cl)Cl.C(Cl)Cl>[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]([S:26][CH3:25])=[C:16]([S:19][C:20]([F:23])([F:22])[F:21])[N:15]=[C:14]1[Cl:24]

Participants

6

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 12232Dimethyl DisulfideHCID 197546641-(2,6-Dichloro-4-trifluoromethylphenyl)-5-amino-2-chloro-4-trifluoromethylsulfenylimidazole

Product 1

HCID 19754616HCID 19754616, compoundYield 58.74%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 700 mg (1.77 mmole) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-amino-2-chloro-4-trifluoromethylsulfenylimidazole in 8 ml of chloroform was added 0.26 ml (2.54 mmole) of dimethyl disulfide and 0.32 ml (0.89 mmole) of t-butylnitrite at 0° C. The resulting mixture was stirred at 0° C. for 15 min. and then at RT for 45 min. The mixture was diluted with 75 ml of methylene chloride and partitioned between water and methylene chloride. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The residue was purified by preparative TLC using 5% ethyl acetate in hexane to give 480 mg (58.74% yield) of the desired product. 1H NMR (CDCl3): δ2.26 (s, 3H), 7.82 (s, 2H).

Workup

  1. waitat RT for 45 min
  2. custompartitioned between water and methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-89c6ca2c73364fc18c6bfb0b88978298
Source dataset
uspto-grants-1993_06
Patent number
US05223525

Reaction notes

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