Hydrochloric Acid → 3-Bromoacetyloxymethyl-5,5-diphenyl-2,4-imidazolidinedione

HRID 359865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 359865
[C:1]1([C:7]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:11][C:10](=[O:12])[N:9]([CH2:13][OH:14])[C:8]2=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:22][CH2:23][C:24](Cl)=[O:25].Cl>C(OCC)C>[Br:22][CH2:23][C:24]([O:14][CH2:13][N:9]1[C:8](=[O:15])[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:11][C:10]1=[O:12])=[O:25]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 89602Bromoacetyl chlorideHCID 1613663-(Hydroxymethyl)phenytoin

Produkt 1

HCID 147506983-Bromoacetyloxymethyl-5,5-diphenyl-2,4-imidazolidinedione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5,5-Diphenyl-3-hydroxymethyl-2,4-imidazolidinedione (2 g, 0.0071 mol) was dissolved in bromoacetylchloride (15 g, 8 mL, 0.096 mol) by heating in an oil bath (70°-80° C. bath temperature) for about 15 minutes, until the formation of HCl ceased. The mixture was cooled and 30 mL of ethyl ether were added. White crystals formed. The mixture was cooled to 0° C., then the crystals were removed by filtration and dried over P2O5. Yield: 2.15 g (75%), m.p. 179°-183° C. Anal. calc. for C18H15N2O4Br: C, 53.61, H, 3.75; N, 6.95; Br, 19.82. Found: C, 53.60; H, 3.79; N, 6.92; Br, 19.90. The product had the formula: ##STR75##

Aufarbeitung

  1. temperatureby heating in an oil bath (70°-80° C. bath temperature) for about 15 minutes
  2. temperatureThe mixture was cooled
  3. customWhite crystals formed
  4. customthe crystals were removed by filtration
  5. dry with materialdried over P2O5

Quellen und Nachweise

ORD-Eintrag
ord-3a825cfd58de44ef942f6ae2a49974a2
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US05002935

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