Dimethylformamide → 1-[4-(2,3-Dihydro-2,2-dimethyl-7-benzofuranylmethyloxy)phenyl]-3,3-dimethylurea

HRID 1032608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1032608
[CH3:1][C:2]1([CH3:13])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11]Cl)[C:4]=2[O:3]1.[OH:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([N:24]([CH3:26])[CH3:25])=[O:23])=[CH:17][CH:16]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][C:2]1([CH3:13])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][O:14][C:15]3[CH:16]=[CH:17][C:18]([NH:21][C:22]([N:24]([CH3:26])[CH3:25])=[O:23])=[CH:19][CH:20]=3)[C:4]=2[O:3]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3014146Urea, N'-(4-hydroxyphenyl)-N,N-dimethyl-HCID 75374857-(Chloromethyl)-2,2-dimethyl-2,3-dihydro-1-benzofuran

Produkt 1

HCID 144998711-[4-(2,3-Dihydro-2,2-dimethyl-7-benzofuranylmethyloxy)phenyl]-3,3-dimethylureaAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3.0 g of 2,3-dihydro-2,2-dimethyl-7-benzofuranylmethyl chloride and 3.0 g of 1-(4-hydroxyphenyl)-3,3-dimethylurea were dissolved into 20 ml of dried N,N-dimethylformamide, and 2.5 g of anhydrous potassium carbonate was added thereto. After the mixture was stirred at 80° C. for 4 hours, the reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with water, it was dried over anhydrous magnesium sulfate and ethyl acetate was distilled off. The residue was subjected to silica gel column chromatography using ethyl acetate/n-hexane (1/1) as a developer to obtain 4.0 g of Compound No. 7 shown in Table 1.

Aufarbeitung

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washAfter the organic layer was washed with water, it
  4. dry with materialwas dried over anhydrous magnesium sulfate and ethyl acetate
  5. distillationwas distilled off

Quellen und Nachweise

ORD-Eintrag
ord-7e4396c81b394f1b8e8329ab0af6ea13
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04959092

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