Tert-Butyl nitrite → HCID 9956748, compound

HRID 2288557Notes

Reaction equation

HRID 2288557 reaction equation
N(OC(C)(C)C)=O.N[C:9]1[C:13]([CH:14]2[CH2:16][C:15]2([Br:18])[Br:17])=[CH:12][N:11]([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])[N:10]=1>O1CCCC1>[Br:18][C:15]1([Br:17])[CH2:16][CH:14]1[C:13]1[CH:9]=[N:10][N:11]([C:19]2[C:24]([Cl:25])=[CH:23][C:22]([C:26]([F:28])([F:29])[F:27])=[CH:21][C:20]=2[Cl:30])[CH:12]=1

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 9913636HCID 9913636, compound

Product 1

HCID 9956748HCID 9956748, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

t-Butyl nitrite (0.12 ml) was added dropwise to a stirred, ice-cooled solution of the title compound of Example 8 (0.25 g) in tetrahydrofuran (5 ml). The reaction mixture was then allowed to warm to room temperature, stirred for 1 hour, heated under reflux for 30 minutes, allowed to cool and partitioned between ether and water. The aqueous phase was separated and extracted with ether, then the combined ether solutions washed with brine, dried (Na2SO4) and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel, using a mixture of hexane:ethyl acetate (9:1) as eluant, furnished the title compound as a colourless oil. δ (CDCl3): 1.85 (t,1H), 2.20 (dd,1H), 2.80 (dd,1H), 7.45 (s,1H), 7.75 (s,2H), 7.78 (s,1H). MS (thermospray): M/Z [M+H] 476.7; C13H7Br2Cl2F3N2 +H requires 476.84.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 30 minutes
  3. temperatureto cool
  4. custompartitioned between ether and water
  5. customThe aqueous phase was separated
  6. extractionextracted with ether
  7. washthe combined ether solutions washed with brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated under reduced pressure
  10. customPurification of the residue by column chromatography on silica gel
  11. additiona mixture of hexane:ethyl acetate (9:1) as eluant

Sources & evidence

ORD record
ord-d604d92c7d394dbda7a266915d101fe7
Source dataset
uspto-grants-2000_07
Patent number
US06090394

Reaction notes

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