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

HRID 2417565Notes

Reaction equation

HRID 2417565 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 (0.21 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-propargyl-phthalimide 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 isopropanol. The resulting precipitate was collected by filtration to give the crude product mp 130°-133° C. 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 isopropanol
  5. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-466c5af9dd7c4a12be26d3e1054d4192
Source dataset
uspto-grants-1984_09
Patent number
US04469633

Reaction notes

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