Tributylphosphine → HCID 10840676, compound

HRID 1277092Notes

Reaction equation

[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[CH:14]=2)=[CH:5][CH:4]=1.[CH2:27]([P:31]([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH3:30]>C1(C)C=CC=CC=1>[Cl-:1].[CH2:36]([P+:31]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[CH:14]=2)=[CH:5][CH:4]=1)[CH2:37][CH2:38][CH3:39]

Participants

Conditions

Temperature: 80 °C

Procedure

In toluene(10 ml) was dissolved (E)-N-[4-(chloromethyl)phenyl]-3-(4-methylphenyl)cinnamamide (300 mg), and to the mixture was added tributylphosphine (248 μl). The mixture was stirred at 80° C. for 3 days and cooled to room temperature. The resulting precipitate was filtered and recrystallized from ethyl acetate-methanol to give (E)tributyl[4-[3-(4-methylphenyl)cinnamamido]benzyl]phosphonium chloride (Compound 78) (389 mg) as colorless crystals.

Workup

temperaturecooled to room temperature
filtrationThe resulting precipitate was filtered
customrecrystallized from ethyl acetate-methanol

Sources & evidence

ORD record: ord-9cc00571ca334109850126426fec42e8
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166006

Reaction notes

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