Triphenylphosphine → 2-methyl-N-{4-[(E)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl}propanamide

HRID 1246435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1246435
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O-]CCCC.[K+].[CH:37]([C:39]1[N:40]=[C:41]([NH:44][C:45](=[O:49])[CH:46]([CH3:48])[CH3:47])[S:42][CH:43]=1)=O>O.C(OCC)(=O)C.CN(C)C=O>[CH3:47][CH:46]([CH3:48])[C:45]([NH:44][C:41]1[S:42][CH:43]=[C:39](/[CH:37]=[CH:8]/[C:7]2[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[N:40]=1)=[O:49]

Komponenten

8

Edukt 4

HCID 11776TriphenylphosphineHCID 660114-Nitrobenzyl bromideHCID 21914786HCID 21914786, VerbindungHCID 23699084Potassium butoxide

Produkt 1

HCID 219151012-methyl-N-{4-[(E)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl}propanamideAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4-nitrobenzyl bromide (381 mg), triphenylphosphine (463 mg) and N,N-dimethylformamide (3 ml) was stirred for 5 hours at room temperature. To the mixture were added potassium butoxide (238 mg) and then N-(4-formyl-1,3-thiazol-2-yl)-2-methylpropanamide (350 mg), and the mixture was stirred for 13 hours at the same temperature. The reaction mixture was poured into ethyl acetate (20 ml) and water (20 ml). The organic layer was washed with water (20 ml), dried over sodium sulfate and concentrated in vacuo. The crystalline residue was collected and washed to give 2-methyl-N-{4-[(E)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl}propanamide (360 mg).

Aufarbeitung

  1. washThe organic layer was washed with water (20 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crystalline residue was collected
  5. washwashed

Quellen und Nachweise

ORD-Eintrag
ord-20e14730fa934a41b1049b758eec4418
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07125901B2

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