Benzene → HCID 15382032, compound

HRID 744087Notes

Reaction equation

HRID 744087 reaction equation
C1([C:7]2[CH:8]=[C:9]([CH:34]=[CH:35][CH:36]=2)[CH:10]=[CH:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20](=[S:33])[C:21]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=3)[CH2:16][CH2:15]2)=O)C=CC=CC=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:46])=CC=1.O.[CH:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>>[C:9]1([C:10]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)=[CH:11][C:12]([N:14]2[CH2:15][CH2:16][N:17]([C:20](=[S:33])[C:21]3[CH:22]=[C:23]([O:31][CH3:32])[C:24]([O:29][CH3:30])=[C:25]([O:27][CH3:28])[CH:26]=3)[CH2:18][CH2:19]2)=[S:46])[CH:34]=[CH:35][CH:36]=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 87949Lawesson's reagent2×HCID 54370034HCID 54370034, compound

Product 1

HCID 15382032HCID 15382032, compound

Procedure

A solution of 1.000 g of 1-(3-phenylcinnamoyl)-4-[3,4,5-trimethoxy(thiobenzoyl)]piperazine (prepared as described in Example 61) in 10 ml of benzene and 0.805 g of Lawesson's Reagent consisting mainly of [2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide] was heated under reflux for 2 hours. At the end of this time, the reaction mixture was cooled to room temperature, poured into water and extracted twice with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and concentrated by distillation under reduced pressure. The residue was purified by column chromatography through 30 g of silica gel eluted with a 3:1 by volume mixture of hexane and ethyl acetate, to give 1.010 g of the title compound as a yellow powder.

Workup

  1. temperatureunder reflux for 2 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated by distillation under reduced pressure
  6. customThe residue was purified by column chromatography through 30 g of silica gel
  7. washeluted with a 3:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-b779df3844ed41539a811463435ea5d8
Source dataset
uspto-grants-1996_09
Patent number
US05559109

Reaction notes

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