Diethylamine → 1-[4-Chloro-2-benzoylphenyl]-3-phthalimidopropyne

HRID 128447Notes

Reaction equation

HRID 128447 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:22]=[CH:23][C:24](I)=[C:25]([CH:34]=1)[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27].C(NCC)C.[CH2:41]([N:44]1[C:48](=[O:49])[C:47]2=[CH:50][CH:51]=[CH:52][CH:53]=[C:46]2[C:45]1=[O:54])[C:42]#[CH:43]>[Pd](Cl)Cl.C(Cl)Cl>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([C:43]#[C:42][CH2:41][N:44]2[C:48](=[O:49])[C:47]3=[CH:50][CH:51]=[CH:52][CH:53]=[C:46]3[C:45]2=[O:54])=[C:25]([C:26](=[O:27])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=1

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 81644N-prop-2-ynylphthalimideHCID 129482625-Chloro-2-iodobenzophenone

Product 1

HCID 128782521-[4-Chloro-2-benzoylphenyl]-3-phthalimidopropyne

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.71 g (4.0 mmole) of palladium chloride, 2.1 g (8.0 mmole) of triphenylphosphine, 0.80 g (4.2 mmole) of cuprous iodide, 68.8 g (0.20 mole) of 5-chloro-2-iodobenzophenone, 200 ml of diethylamine, and 400 ml of methylene chloride was stirred at room temperature under argon until complete solution was obtained. In one portion, 40.0 g (0.22 mole) of N-propargylphthalimide was added to the solution and the resulting mixture stirred for 20 hr. The volatiles were removed at reduced pressure and the residue was triturated with 200 ml of iospropanol. The resulting precipitate was collected by filtration to give crude end product. Recrystallization from acetone gave cream colored prisms, mp 148°-150° C.

Workup

  1. customwas obtained
  2. stirringthe resulting mixture stirred for 20 hr
  3. customThe volatiles were removed at reduced pressure
  4. customthe residue was triturated with 200 ml of iospropanol
  5. filtrationThe resulting precipitate was collected by filtration
  6. customto give crude end product
  7. customRecrystallization from acetone
  8. customgave cream colored prisms, mp 148°-150° C.

Sources & evidence

ORD record
ord-48a9bbd706104548b506c02d8a39b732
Source dataset
uspto-grants-1981_03
Patent number
US04259503

Reaction notes

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