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

HRID 1888665Notes

Reaction equation

HRID 1888665 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-d7b2828292a44a1fb4e7db288680ecce
Source dataset
uspto-grants-2013_08
Patent number
US08501794B2

Reaction notes

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