Iodine → HCID 68917779, compound

HRID 1455281Notes

Reaction equation

HRID 1455281 reaction equation
II.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C:29]([NH:32][NH:33][C:34](=O)[CH2:35][N:36]1[C:40]([CH2:41][CH3:42])=[C:39]([O:43][C:44]2[CH:49]=[CH:48][C:47]([C:50]#[N:51])=[CH:46][CH:45]=2)[C:38]([CH2:52][CH3:53])=[N:37]1)(=[O:31])[CH3:30]>ClCCl>[CH2:52]([C:38]1[C:39]([O:43][C:44]2[CH:45]=[CH:46][C:47]([C:50]#[N:51])=[CH:48][CH:49]=2)=[C:40]([CH2:41][CH3:42])[N:36]([CH2:35][C:34]2[O:31][C:29]([CH3:30])=[N:32][N:33]=2)[N:37]=1)[CH3:53]

Participants

6

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 68955800HCID 68955800, compound

Product 1

HCID 68917779HCID 68917779, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Iodine (243 mg, 0.95 mmol) was added portionwise to a solution of triphenylphosphine (250 mg, 0.95 mmol) in dichloromethane (10 ml). The reaction mixture was then stirred for 10 minutes, after which time triethylamine (194 mg, 1.9 mmol) was added, followed by the acetylacetohydrazide of step (b) above (170 mg, 0.48 mmol). The reaction mixture was then stirred at room temperature for 12 hours after which time it was evaporated to dryness and purified by flash chromatography on silica gel eluting with ethyl acetate:pentane (1:1, by volume) to provide the title compound (80 mg, 49%) as 4:1 mixture product:triphenylphosphine oxide.

Workup

  1. stirringThe reaction mixture was then stirred at room temperature for 12 hours after which time it
  2. customwas evaporated to dryness
  3. custompurified by flash chromatography on silica gel eluting with ethyl acetate:pentane (1:1, by volume)

Sources & evidence

ORD record
ord-ff215c6ed98b4e9f8a1878e1525d3345
Source dataset
uspto-grants-2009_01
Patent number
US07482375B2

Reaction notes

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