Bromoform → HCID 9893969, compound

HRID 376224Notes

Reaction equation

HRID 376224 reaction equation
C(Br)(Br)[Br:2].N[C:6]1[C:10]([CH:11]2[CH2:13][C:12]2([Br:15])[Br:14])=[CH:9][N:8]([C:16]2[C:21]([Cl:22])=[CH:20][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:18][C:17]=2[Cl:27])[N:7]=1.N(OC(C)(C)C)=O>C(#N)C>[Br:2][C:6]1[C:10]([CH:11]2[CH2:13][C:12]2([Br:15])[Br:14])=[CH:9][N:8]([C:16]2[C:21]([Cl:22])=[CH:20][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:18][C:17]=2[Cl:27])[N:7]=1

Participants

5

Reactant 3

HCID 5558BromoformHCID 10906Tert-Butyl nitriteHCID 9913636HCID 9913636, compound

Product 1

HCID 9893969HCID 9893969, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Bromoform (2 ml) was added to a stirred solution of the title compound of Example 8 (0.25 g) in acetonitrile (2 ml) and the mixture cooled to about 0° C. t-Butyl nitrite was added dropwise, then the reaction mixture allowed to warm to room temperature, stirred for 1 hour at room temperature and then for 1 hour under reflux, allowed to cool and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using mixtures of hexane:ether (19:1 then 9:1) as eluants, to provide the title compound as a colourless gum. δ (CDCl3): 1.85 (t,1H), 2.25 (dd,1H), 2.70 (dd,1H), 7.25 (s,1H), 7.70 (s,2H). MS (thermospray): M/Z [M+H] 554.5; C13H6Br3Cl2F3N2 +H reqires 554.75.

Workup

  1. additionwas added dropwise
  2. temperaturefor 1 hour under reflux
  3. temperatureto cool
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b5d311d34db9486ebcc4eccc978dfbb6
Source dataset
uspto-grants-2000_02
Patent number
US06019986

Reaction notes

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