Cyanamide → Methyl N-cyanobutanimidate

HRID 248613Notes

Reaction equation

HRID 248613 reaction equation
Cl.[C:2](=[NH:8])([O:6][CH3:7])[CH2:3][CH2:4][CH3:5].[N:9]#[C:10]N.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>>[C:10]([N:8]=[C:2]([O:6][CH3:7])[CH2:3][CH2:4][CH3:5])#[N:9]

Participants

4

Reactant 3

HCID 9864CyanamideHCID 24243Trisodium PhosphateHCID 12657464Methyl butanimidate--hydrogen chloride (1/1)

Product 1

HCID 15477524Methyl N-cyanobutanimidateYield 87.4%

Procedure

The methyl butyrimidate salt from Example 1 (322 g, 2.34 mol) was dissolved in a 50% aqueous solution of cyanamide (236 g, 2.81 mol) and cooled in an ice bath. Dibasic sodium phosphate (164 g, 1.15 mol) was added to the reaction mixture in portions over a period of 1 hour. The resulting suspension was stirred at room temperature for 2 hours and the liquid decanted from the reaction mixture. The remaining solid was diluted with water (2 L) and extracted with ether (3×600 mL). The combined organic layers were washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue distilled under high vacuum to afford 258 g of methyl N-cyanobutyrimidate. MS (DEI) 127 (M+1).

Workup

  1. temperaturecooled in an ice bath
  2. customthe liquid decanted from the reaction mixture
  3. additionThe remaining solid was diluted with water (2 L)
  4. extractionextracted with ether (3×600 mL)
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. distillationthe residue distilled under high vacuum

Sources & evidence

ORD record
ord-9a300569d83a4d2ca2f3749d371dc958
Source dataset
uspto-grants-1993_05
Patent number
US05210211

Reaction notes

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