Diphenylamine → HCID 18548219, compound

HRID 1265992Notes

Reaction equation

HRID 1265992 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Li].CS(O[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]1[CH2:30][CH:29]=1)(=O)=O>C1COCC1>[C:8]1([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]2[CH2:30][CH:29]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 11487DiphenylamineHCID 18548198HCID 18548198, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 18548219HCID 18548219, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diphenylamine (0.42 g, 2.5 mmol) in 10 ml of THF was cooled to −78° C. and treated with 1.6 ml (1.4M, 2.2 mmol) methyllithium. 1-(7-Methanesulfonyloxyheptyl)-cyclopropene was added, the bath was removed, and the reaction mixture was allowed to warm to room temperature. The reaction was held for 5.5 hours, then quenched with water. Ether and water were added to the reaction mixture and the phases were separated. The ether phase was washed with water twice, washed with brine, dried over magnesium sulfate and stripped. The product was chromatographed to give 80 mg of 7-(diphenylamino)-1-heptylcyclopropene as a colorless liquid.

Workup

  1. customthe bath was removed
  2. customquenched with water
  3. additionEther and water were added to the reaction mixture
  4. customthe phases were separated
  5. washThe ether phase was washed with water twice
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. customThe product was chromatographed

Sources & evidence

ORD record
ord-653409149fe74eb682f0beeac6105ede
Source dataset
uspto-grants-2003_04
Patent number
US06548448B2

Reaction notes

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