Triethylamine → 1-(N-methoxy-N-methylcarbamoyl)-3-(3,5-dichlorophenyl)-hydantoin

HRID 1834904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1834904
C(N(CC)CC)C.[CH3:8][N:9]([O:13][CH3:14])[C:10](Cl)=[O:11].[Cl:15][C:16]1[CH:17]=[C:18]([N:23]2[C:27](=[O:28])[CH2:26][NH:25][C:24]2=[O:29])[CH:19]=[C:20]([Cl:22])[CH:21]=1>O1CCCC1>[CH3:14][O:13][N:9]([CH3:8])[C:10]([N:25]1[CH2:26][C:27](=[O:28])[N:23]([C:18]2[CH:17]=[C:16]([Cl:15])[CH:21]=[C:20]([Cl:22])[CH:19]=2)[C:24]1=[O:29])=[O:11]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 1686913-(3,5-Dichlorophenyl)-2,4-imidazolidinedioneHCID 2734926N-methoxy-N-methylcarbamoyl chloride

Produkt 1

HCID 203728431-(N-methoxy-N-methylcarbamoyl)-3-(3,5-dichlorophenyl)-hydantoin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

At about 20° C, 10.5 parts of triethylamine and subsequently 12.4 parts of methylmethoxycarbamoyl chloride are added to a suspension of 24.5 parts of 3-(3,5-dichlorophenyl)-hydantoin in 250 parts of dry tetrahydrofuran. After all has been added, the mixture is refluxed for 3 hours. After the mixture has been cooled to 20° C, the precipitated triethylamine hydrochloride is removed by suction filtration. The filtrate is concentrated. The residue is dissolved in a 1:1 mixture of n-pentane and ether, suction filtered, dried and recrystallized from toluene.

Aufarbeitung

  1. additionAfter all has been added
  2. temperaturethe mixture is refluxed for 3 hours
  3. customthe precipitated triethylamine hydrochloride is removed by suction filtration
  4. concentrationThe filtrate is concentrated
  5. dissolutionThe residue is dissolved in a 1:1 mixture of n-pentane and ether, suction
  6. filtrationfiltered
  7. customdried
  8. customrecrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-5e855e15c4e64fbeae8ff548032757d8
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04071685

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