Hydrochloric Acid → N-[2-(2-ethoxyethoxy)-phenyl-sulfonyl]-N'-(4-difluoromethoxy-6-methylpyrimidin-2-yl)-urea

HRID 1633347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633347
O([C:8]([NH:10][C:11]1[N:16]=[C:15]([O:17][CH:18]([F:20])[F:19])[CH:14]=[C:13]([CH3:21])[N:12]=1)=[O:9])C1C=CC=CC=1.[CH2:22]([O:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34]([NH2:37])(=[O:36])=[O:35])[CH3:23].N12CCCCC1C=NCCC2.Cl>C(#N)C.O.C(OCC)(=O)C>[CH2:22]([O:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34]([NH:37][C:8]([NH:10][C:11]1[N:16]=[C:15]([O:17][CH:18]([F:19])[F:20])[CH:14]=[C:13]([CH3:21])[N:12]=1)=[O:9])(=[O:35])=[O:36])[CH3:23]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 201856962-(Ethoxy-ethoxy)-benzenesulfonamideHCID 221041722-Phenoxycarbonylamino-4-difluoromethoxy-6-methyl-pyrimidine

Produkt 1

HCID 53940140N-[2-(2-ethoxyethoxy)-phenyl-sulfonyl]-N'-(4-difluoromethoxy-6-methylpyrimidin-2-yl)-urea

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3.5 g of 2-phenoxycarbonylamino-4-difluoromethoxy-6-methyl-pyrimidine (crude product) and 2.9 g of 2-(ethoxy-ethoxy)-benzenesulfonamide in 100 ml of absolute acetonitrile is decomposed with 1.8 g of 1,5-diazabicyclo[5.4.0]undec-5-ene; it is then stirred for 1 hour at 20° to 25° C., diluted with 500 ml of water and acidified with hydrochloric acid. The precipitated oil is taken up with 200 ml of ethyl acetate, dried over sodium sulfate and concentrated by evaporation. Crystallisation of the oily residue from diethyl ether and acetone yields, as colourless crystals, N-[2-(2-ethoxy-ethoxy)-phenyl-sulfonyl]-N'-(4-difluoromethoxy-6-methyl-pyrimidin-2-yl)-urea, m.p. 90° to 95° C. (decomposition); yield 2.7 g.

Aufarbeitung

  1. dry with materialdried over sodium sulfate
  2. concentrationconcentrated by evaporation
  3. customCrystallisation of the oily residue from diethyl ether and acetone

Quellen und Nachweise

ORD-Eintrag
ord-8091d18f191449af81835a836d00e8b3
Quelldatensatz
uspto-grants-1984_10
Patentnummer
US04480101

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