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Phosgene → N,N-Dimethyl-2-{N-[N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl}-4-nitrobenzamide

HRID 840344
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 840344
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[N:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[N:7]=1.C(N(CCCC)CCCC)CCC.[CH3:29][N:30]([CH3:46])[C:31](=[O:45])[C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][C:33]=1[S:41]([NH2:44])(=[O:43])=[O:42].[OH-].[K+]>C(OCC)(=O)C.O>[CH3:29][N:30]([CH3:46])[C:31](=[O:45])[C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][C:33]=1[S:41]([NH:44][C:1]([NH:5][C:6]1[N:7]=[C:8]([O:14][CH3:15])[CH:9]=[C:10]([O:12][CH3:13])[N:11]=1)=[O:2])(=[O:42])=[O:43]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 6371PhosgeneHCID 7622Tributylamine2×HCID 14797Potassium HydroxideHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 22066001N,N-Dimethyl-4-nitro-2-sulfamoylbenzamide

Produkt 1

HCID 15335261
N,N-Dimethyl-2-{N-[N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl}-4-nitrobenzamide
Ausbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel3×

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

Phosgene (23 g, 232 mmol) was passed into ethyl acetate (250 ml) at 10° C. A solution of 2-amino-4,6-dimethoxypyrimidine (20 g, 129 mmol) and tributylamine (47.82 g, 258 mmol) in ethyl acetate (270 ml) was added dropwise in the course of 3 h. 15 min after the addition, the jacket was warmed to 30° C. and ethyl acetate and excess phosgene were distilled off in vac. The remaining solution of the isocyanate was cooled to 10° C. and added dropwise to a suspension of N,N-dimethyl-2-aminosulfonyl-4-nitro-benzamide (31.7 g, 116 mmol) and tributylamine (22.96 g, 232 mmol) in ethyl acetate (100 ml) at 20° C. in the course of 3 h. The mixture was stirred for 1 h and treated with water (300 ml) and potassium hydroxide solution (10% strength, 240 ml). After phase separation, the organic phase was extracted with water (50 ml). The combined aqueous phases were extracted with ethyl acetate (50 ml) and adjusted to pH 2 to 3 using 6M hydrochloric acid. After filtering off the product, washing with water (2×100 ml) and drying, 49.09 g (85.8% of theory) of N,N-dimethyl-2{-N-[N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl}-4-nitrobenz-amide were obtained.

Aufarbeitung

  1. addition15 min after the addition
  2. distillationethyl acetate and excess phosgene were distilled off in vac
  3. temperatureThe remaining solution of the isocyanate was cooled to 10° C.
  4. customAfter phase separation
  5. extractionthe organic phase was extracted with water (50 ml)
  6. extractionThe combined aqueous phases were extracted with ethyl acetate (50 ml)
  7. filtrationAfter filtering off the product
  8. washwashing with water (2×100 ml)
  9. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-fe67b2109c164e97b9d545d15cabb50f
Quelldatensatz
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06365739B1

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