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Benzyl Bromide → 2-(Benzyloxycarbonyl)-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

HRID 1074957
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1074957
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]([NH:12][S:13]([C:16]2[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=2[C:18]([OH:20])=[O:19])(=[O:15])=[O:14])=[O:11])[N:3]=1.C(N(CC)CC)C.[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCCC1>[CH2:32]([O:19][C:18]([C:17]1[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=1[S:13]([NH:12][C:10]([NH:9][C:4]1[N:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[N:3]=1)=[O:11])(=[O:15])=[O:14])=[O:20])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 52998Sulfometuron

Produkt 1

HCID 131765802-(Benzyloxycarbonyl)-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To 1.75 g of 2-(4,6-dimethylpyrimidin-2-ylaminocarbonylsulfamoyl) benzoic acid was added 0.51 g of triethylamine in 10 ml tetrahydrofuran and 0.88 g of benzyl bromide in 10 ml of tetrahydrofuran. The mixture was heated to reflux for 1.5 hours, filtered and the tetrahydrofuran evaporated in-vacuo. The residue was extracted with hot 1-chlorobutane, diluted with ethyl acetate, washed with water and saturated aqueous sodium bicarbonate. The organic phase was dried over magnesium sulfate, filtered and the solvents evaporated in-vacuo. The resultant residue was crystallized from 1-chlorobutane to a melting point of 157°. This product showed absorption peaks in the infrared region at 1720, 1600, 1560 cm-1 consistent for the desired ester and absorption by nuclear magnetic resonance at 2.45δ, singlet, for CH3 ; 5.3δ singlet, CH2 on benzyl; 6.65δ singlet CH of pyrimidine and aryl peaks at 7-8δ.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. filtrationfiltered
  4. customthe tetrahydrofuran evaporated in-vacuo
  5. extractionThe residue was extracted with hot 1-chlorobutane
  6. additiondiluted with ethyl acetate
  7. washwashed with water and saturated aqueous sodium bicarbonate
  8. dry with materialThe organic phase was dried over magnesium sulfate
  9. filtrationfiltered
  10. customthe solvents evaporated in-vacuo
  11. customThe resultant residue was crystallized from 1-chlorobutane to a melting point of 157°
  12. customabsorption peaks in the infrared region at 1720, 1600, 1560 cm-1
  13. customconsistent for the desired ester and absorption by nuclear magnetic resonance at 2.45δ, singlet

Quellen und Nachweise

ORD-Eintrag
ord-fca96dd8705940d2be899888d106119c
Quelldatensatz
uspto-grants-1983_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04394506

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