Water → 3-(2-(4-(2-Methylbenzoyl)-3-chlorophenylamino)phenyl)-1,1-dimethylurea

HRID 428299

Reaktionsgleichung

Reaktionsgleichung von HRID 428299
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:23]=[CH:22][C:12]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[O:14])=[C:11]([Cl:24])[CH:10]=1.[CH3:25][N:26]([CH3:30])[C:27](Cl)=[O:28].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:13]([C:12]1[CH:22]=[CH:23][C:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:27](=[O:28])[N:26]([CH3:30])[CH3:25])=[CH:10][C:11]=1[Cl:24])=[O:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 98191574-(2-Aminophenylamino)-2-chloro-2'-methylbenzophenone2×

Produkt 1

HCID 183582303-(2-(4-(2-Methylbenzoyl)-3-chlorophenylamino)phenyl)-1,1-dimethylurea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(2-aminophenylamino)-2-chloro-2′-methylbenzophenone (Compound 156, 1.2 g, 3.5 mmol), dimethylcarbamyl chloride (0.32 ml, 3.5 mmol) and potassium carbonate (1.0 g, 7 mmol) in N,N-dimethylformamide (20 ml) was stirred at room temperature for 16 hours. The reaction mixture was poured into water (100 ml) and was extracted with ethyl acetate (3×75 ml). The organic phase was dried (MgSO4), filtered and evaporated in vacuo to give the crude product. The crude product was purified by flash chromatography by using ethyl acetate/pentane mixtures from 1:9 to 1:1. Trituration with diethyl ether/pentane 1:1 afforded the pure title compound.

Aufarbeitung

  1. extractionwas extracted with ethyl acetate (3×75 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto give the crude product
  6. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0855c01a97c84672bc59d2dbeca8681d
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313174B1

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