Hydrochloric Acid → N-(4-azidophenylsulfonyl)-N'-(4-methoxy-6-methylpyrimidin-2-yl)urea

HRID 1583878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1583878
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([N:10](C2C=CC=CC=2)[C:11](=[O:13])[O-])[N:4]=1.[N:20]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1)=[N+:21]=[N-:22].N12CCCCC1C=NCCC2.Cl>O1CCOCC1.O>[N:20]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:32][C:11]([NH:10][C:5]2[N:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([CH3:9])[N:6]=2)=[O:13])(=[O:30])=[O:31])=[CH:25][CH:24]=1)=[N+:21]=[N-:22]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 35585904-AzidobenzenesulfonamideHCID 18954641N-(4-methoxy-6-methylpyrimidin-2-yl)phenylcarbamate

Produkt 1

HCID 23320462N-(4-azidophenylsulfonyl)-N'-(4-methoxy-6-methylpyrimidin-2-yl)ureaAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

A solution of 2.9 g of N-(4-methoxy-6-methylpyrimidin-2-yl)phenylcarbamate in 10 ml of dioxan is added dropwise at 20°-25° C. to a solution of 2 g of 4-azidophenylsulfonamide and 1.6 ml of 1,5-diazabicyclo(5,4,0)-undec-5-ene in 20 ml of dioxan and the mixture is stirred for 3 hours at the same temperature. The reaction mixture is then taken up in 200 ml of water and the aqueous mixture is then acidified with hydrochloric acid to pH 2. The precipitated product is isolated, washed with ethyl acetate and dried, affording N-(4-azidophenylsulfonyl)-N'-(4-methoxy-6-methylpyrimidin-2-yl)urea in 67% yield in the form of greenish crystals with a melting point of 192° C.

Aufarbeitung

  1. customThe precipitated product is isolated
  2. washwashed with ethyl acetate
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2f73f91e51ff48b8ab8d1e842be3d9db
Quelldatensatz
uspto-grants-1985_11
Patentnummer
US04555262

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