Methanol → 6-(2-{1-[5-(3,4-Dichlorophenyl)-4-hydroxythiophen-3-yl]ethylidene}hydrazinecarbothioamido)-2,3-dihydrobenzo[1,4]dioxine

HRID 1094938

Reaktionsgleichung

Reaktionsgleichung von HRID 1094938
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[S:10][CH:11]=[C:12]([C:15](=[N:17][NH2:18])[CH3:16])[C:13]=2[OH:14])[CH:5]=[CH:6][C:7]=1[Cl:8].[N:19]([C:22]1[CH:31]=[CH:30][C:25]2[O:26][CH2:27][CH2:28][O:29][C:24]=2[CH:23]=1)=[C:20]=[S:21].CO.O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[S:10][CH:11]=[C:12]([C:15](=[N:17][NH:18][C:20](=[S:21])[NH:19][C:22]3[CH:31]=[CH:30][C:25]4[O:26][CH2:27][CH2:28][O:29][C:24]=4[CH:23]=3)[CH3:16])[C:13]=2[OH:14])[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 27761732,3-Dihydro-1,4-benzodioxin-6-yl isothiocyanateHCID 714052582-(3,4-Dichlorophenyl)-4-(1-hydrazinylideneethyl)thiophene-3-ol

Produkt 1

HCID 732999586-(2-{1-[5-(3,4-Dichlorophenyl)-4-hydroxythiophen-3-yl]ethylidene}hydrazinecarbothioamido)-2,3-dihydrobenzo[1,4]dioxineAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(3,4-Dichlorophenyl)-4-(1-hydrazonoethyl)-thiophen-3-ol (25 mg, 0.08 mmol) prepared in Reference Synthetic Example 13 in dimethylformamide (0.25 mL) was stirred with 6-isothiocyanato-2,3-dihydrobenzo[1,4]dioxine (24 mg, 0.13 mmol, at 30° C. for 4 hours. Methanol and water were added to the reaction solution, and the resulting crystals were collected by filtration, washed and dried to give 28 mg of the desired product (yield 65%).

Aufarbeitung

  1. filtrationthe resulting crystals were collected by filtration
  2. washwashed
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9fc6e5d3ea8c48748f42dc337b9e83c2
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08134013B2

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