Triethylamine → 1-(Dichlorofluoromethylthio)-3-(3'-chloro-4'-methylphenyl)-imidazolidine-2,4-dione

HRID 1657459Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1657459
[F:1][C:2]([Cl:6])([Cl:5])[S:3]Cl.[Cl:7][C:8]1[CH:9]=[C:10]([N:15]2[C:19](=[O:20])[CH2:18][NH:17][C:16]2=[O:21])[CH:11]=[CH:12][C:13]=1[CH3:14].C(N(CC)CC)C>C(OC(=O)C)C>[Cl:5][C:2]([Cl:6])([F:1])[S:3][N:17]1[CH2:18][C:19](=[O:20])[N:15]([C:10]2[CH:11]=[CH:12][C:13]([CH3:14])=[C:8]([Cl:7])[CH:9]=2)[C:16]1=[O:21]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 759261,1-Dichloro-1-fluoromethanesulfenyl chlorideHCID 214894803-(3'-Chloro-4'-methylphenyl)imidazolidine-2,4-dione

Produkt 1

HCID 214894771-(Dichlorofluoromethylthio)-3-(3'-chloro-4'-methylphenyl)-imidazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel3×

Versuchsvorschrift

23.8 g of fluorodichloromethanesulphenyl chloride in 100 ml of acetic acid ethyl ester is added dropwise within 20 minutes at -10°C, with vigorous stirring, to a suspension of 22.5 g of 3-(3'-chloro-4'-methylphenyl)imidazolidine-2,4-dione in 400 ml of acetic acid ethyl ester, and after one hour there is also added dropwise, at 0°C in the course of 10 minutes, 14.2 g of triethylamine in 100 ml of acetic acid ethyl ester; the cooling bath is subsequently removed and stirring is continued for 3 hours at room temperature. The triethylamine hydrochloride that has precipitated is filtered off and then washed with 100 ml of acetic acid ethyl ester; the solvent is evaporated off in vacuo to obtain, after recrystallisation in methanol, Compound No. 1 which melts at 166° - 167°C.

Aufarbeitung

  1. customthe cooling bath is subsequently removed
  2. customThe triethylamine hydrochloride that has precipitated
  3. filtrationis filtered off
  4. washwashed with 100 ml of acetic acid ethyl ester
  5. customthe solvent is evaporated off in vacuo
  6. customto obtain
  7. customafter recrystallisation in methanol

Quellen und Nachweise

ORD-Eintrag
ord-d07cb8d2e1b64b3aaa8d0f6fa94b79ae
Quelldatensatz
uspto-grants-1976_06
Patentnummer
US03960883

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