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Phosgene → Ethoxysulfuron

HRID 840342
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 840342
[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(CC)CC)C.[CH2:23]([O:25][C:26]1[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=1[O:28][S:29]([NH2:32])(=[O:31])=[O:30])[CH3:24]>C(OCC)(=O)C.O>[CH3:13][O:12][C:10]1[CH:9]=[C:8]([O:14][CH3:15])[N:7]=[C:6]([NH:5][C:1](=[O:2])[NH:32][S:29]([O:28][C:27]2[CH:33]=[CH:34][CH:35]=[CH:36][C:26]=2[O:25][CH2:23][CH3:24])(=[O:31])=[O:30])[N:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6371Phosgene2×HCID 8471Triethylamine2×HCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 145806752-Ethoxyphenyl sulfamate

Produkt 1

HCID 3623881Ethoxysulfuron

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962Water
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel4×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

Ethyl acetate (16 ml) was introduced and cooled to −10° C. under nitrogen. Phosgene (4.0 g, 0.04 mol) was passed in at this temperature and then a solution of 2-amino-4,6dimethoxypyrimidine (2.86 g, 0.0185 mol) and triethylamine (3.73 g, 0.037 mol) in ethyl acetate (20 ml) was added dropwise in the course of 2 h. After 1 h, the reaction was warmed to 20° C., nitrogen was blown through until there was no longer phosgene in the solution, and then a solution of 2-ethoxyphenoxysulfonamide (4.0 g, 0.0184 mol) in ethyl acetate (10 ml) and triethylamine (1.86 g, 0.0184 mol) in ethyl acetate (10 ml) were successively added dropwise in the course of 30 min. After 30 min, water (100 ml) was added, the phases were separated and the organic phase was extracted with 2×25 ml of 1.5M sodium hydroxide solution. The aqueous phases were combined, washed with xylene (20 ml), adjusted to pH=2 using 6M hydrochloric acid and the product was filtered off and dried; yield: 5.57 g, 70.7% of theory.

Aufarbeitung

  1. temperaturethe reaction was warmed to 20° C.
  2. waitAfter 30 min
  3. customthe phases were separated
  4. extractionthe organic phase was extracted with 2×25 ml of 1.5M sodium hydroxide solution
  5. washwashed with xylene (20 ml)
  6. filtrationthe product was filtered off
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-473ef57d8f1e42a2bc4a143b6eac40a0
Quelldatensatz
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06365739B1

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