Ammonia → Aminocyclopyrachlor-methyl

HRID 249659Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 249659
[NH2:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:5]=[C:4]([C:11]([OH:13])=[O:12])[C:3]=1[Cl:14].S(Cl)(Cl)=O.O.N.[CH3:21]O>S(=O)(=O)(O)O>[NH2:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:5]=[C:4]([C:11]([O:13][CH3:21])=[O:12])[C:3]=1[Cl:14]

Komponenten

7

Edukt 5

HCID 222AmmoniaHCID 887MethanolHCID 962WaterHCID 24386Thionyl ChlorideHCID 17747875Aminocyclopyrachlor2×

Produkt 1

HCID 16725794Aminocyclopyrachlor-methyl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidKatalysator

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a solution of 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (i.e. the product of Step D1 or D2 of Example 2) (2.0 g, 8.5 mmol) in methanol (20 mL) was added dropwise thionyl chloride (4 mL, 70 mmol). The mixture was heated at reflux for 24 h. Concentrated sulfuric acid (5 drops) was added, and the reaction mixture was heated at reflux for 16 h. After the mixture was cooled, water (30 mL) was added, and aqueous ammonia (28%, 10 mL) was added dropwise. The mixture was cooled to 5° C., and the solid was isolated by filtration, washed with water and dried in a vacuum oven at 40° C. to afford the title product (2.3 g), a compound of the present invention.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 h
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 16 h
  5. temperatureAfter the mixture was cooled
  6. customthe solid was isolated by filtration
  7. washwashed with water
  8. customdried in a vacuum oven at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-55af0cb4747e42688cbc36ab4b90fef9
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863220B2

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