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Carbon tetrabromide → 2,6-dichloro-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyl bromide

HRID 365555
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 365555
[Cl:1][C:2]1[C:7]([N:8]([CH3:27])[C:9](=[O:26])[CH2:10][NH:11][C:12](=[O:25])[CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:24])[NH:22][CH3:23])=[CH:17][CH:16]=2)=[CH:6][CH:5]=[C:4]([Cl:28])[C:3]=1[CH2:29]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:51]>ClCCl>[Cl:1][C:2]1[C:7]([N:8]([CH3:27])[C:9](=[O:26])[CH2:10][NH:11][C:12](=[O:25])[CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:24])[NH:22][CH3:23])=[CH:17][CH:16]=2)=[CH:6][CH:5]=[C:4]([Cl:28])[C:3]=1[CH2:29][Br:51]
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Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromide2×HCID 11776Triphenylphosphine2×HCID 540364432,6-dichloro-1-hydroxymethyl-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]-benzene

Produkt 1

HCID 538052362,6-dichloro-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyl bromideAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a mixture of 2,6-dichloro-1-hydroxymethyl-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzene (8.10 g) in dichloromethane (81 ml) was added triphenylphosphine (5.66 g) and carbon tetrabromide (8.95 g) at 0° C. After 15 minutes the reaction mixture was stirred at ambient temperature for 3 hours. To the mixture was added triphenylphosphine (1.42 g) and carbon tetrabromide (2.39 g) and stirred for another 2 hours. The reaction mixture was washed with saturated sodium hydrogen carbonate, water and brine. After dried over anhydrous magnesium sulfate, the mixture was filtered and evaporated in vacuo. The residue was purified by flash column chromatography eluting with dichloromethane:ethyl acetate (1:1, V/V) and dichloromethane:methanol (20:1, V/V) followed by crystallizing from ethyl acetate to give 2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyl bromide (6.40 g) as pale yellow crystals.

Aufarbeitung

  1. stirringstirred for another 2 hours
  2. washThe reaction mixture was washed with saturated sodium hydrogen carbonate, water and brine
  3. dry with materialAfter dried over anhydrous magnesium sulfate
  4. filtrationthe mixture was filtered
  5. customevaporated in vacuo
  6. customThe residue was purified by flash column chromatography
  7. washeluting with dichloromethane:ethyl acetate (1:1, V/V) and dichloromethane:methanol (20:1, V/V)
  8. customby crystallizing from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ff3e46c47f864c12ad774ad3b691326d
Quelldatensatz
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06127389

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