Cyanamide → Ethyl 5-chloro-N-cyano-2-methoxybenzimidate

HRID 76295

Reaktionsgleichung

Reaktionsgleichung von HRID 76295
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([O:14][CH3:15])=[C:7]([CH:13]=1)[C:8](=[NH:12])[O:9][CH2:10][CH3:11].O.OP([O-])(O)=O.[Na+].O.O.O.O.O.O.O.OP([O-])([O-])=O.[Na+].[Na+].[N:37]#[C:38]N>CC#N.O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([O:14][CH3:15])=[C:7]([CH:13]=1)[C:8](=[N:12][C:38]#[N:37])[O:9][CH2:10][CH3:11]

Komponenten

7

Edukt 4

HCID 9864CyanamideHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 6096963Phosphoric acid, disodium salt, heptahydrateHCID 66851771Ethyl 5-chloro-2-methoxybenzimidate hydrochloride

Produkt 1

HCID 86623446Ethyl 5-chloro-N-cyano-2-methoxybenzimidateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of ethyl 5-chloro-2-methoxybenzimidate (1.3 g, 6.2 mmol, obtained after aqueous bicarbonate wash of Example 128C) in MeCN (2 mL) was added to a solution of sodium phosphate monobasic monohydrate (3.4 g, 24.7 mmol), sodium phosphate dibasic heptahydrate (3.3 g, 12.4 mmol) and cyanamide (0.52 g, 12.4 mmol) in water (20 mL). The reaction mixture was stirred at room temperature overnight and then extracted with dichloromethane (3×15 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue contained about 30% of starting material. The residue was reprocessed with half the amounts of the reagents to drive the reaction to completion and that yielded 1.32 g (90%) of the title compound. MS (ESI+) m/z 239 (M+H)+.

Aufarbeitung

  1. extractionextracted with dichloromethane (3×15 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe reaction to completion

Quellen und Nachweise

ORD-Eintrag
ord-fe6bedb05c764f489000b06c81fddb89
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835475B2

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