Butyl nitrite → HCID 21439841, compound

HRID 328711Notes

Reaction equation

HRID 328711 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:11]=2N)=[CH:5][CH:4]=1.N(OCCCC)=O>C(O)(=O)C.[Cu]>[F:2][C:3]1[CH:8]=[CH:7][C:6]2[S:9][C:10]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:11]=3[C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 10996Butyl nitriteHCID 21439837HCID 21439837, compound

Product 1

HCID 21439841HCID 21439841, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 176Acetic AcidSolvent2×

Conditions

Temperature
11 °C

Procedure

To a stirred suspension of 55 g. (0.183 mole) of 2-(4-fluorophenylthio)-5-nitroaniline hydrochloride in 450 ml. of acetic acid at 16 to 18° C. is added dropwise 18.6 g. (0.181 mole of n-butyl nitrite during a period of 20 minutes. The solution is then diluted with 1.5 liters of cold (12° C.) of 50 percent aqueous acetic acid. The solution is maintained at 10 to 12° C., and 68 g. of copper powder are added in small portions during a period of 15 minutes. After stirring at 10° to 15° C. for an additional 20 minutes, the mixture is heated and stirred at 50° C. for 1 hour. The mixture is cooled to 5° C. and filtered. The solid residue is washed thrice with 300 ml. of aqueous sodium hydroxide, then thrice with 300 ml. of distilled water. The brown solid is dissolved in hot benzene, filtered and the hot filtrate treated with decolorizing charcoal. The benzene is evaporated to give a residue which is twice recrystallized from benzene to give off-white crystals of 2-fluoro- 8-nitrodibenzothiophene, m.p. 200°-202° C.

Workup

  1. additionTo a stirred suspension of 55 g
  2. temperaturethe mixture is heated
  3. stirringstirred at 50° C. for 1 hour
  4. temperatureThe mixture is cooled to 5° C.
  5. filtrationfiltered
  6. washThe solid residue is washed thrice with 300 ml
  7. dissolutionThe brown solid is dissolved in hot benzene
  8. filtrationfiltered
  9. additionthe hot filtrate treated with decolorizing charcoal
  10. customThe benzene is evaporated
  11. customto give a residue which
  12. customis twice recrystallized from benzene

Sources & evidence

ORD record
ord-e6c7dbcd2eb44d8584f53a52ddc38534
Source dataset
uspto-grants-1977_04
Patent number
US04018780

Reaction notes

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