Cyanoacetic acid → HCID 10607908, compound

HRID 2226145Notes

Reaction equation

HRID 2226145 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].C1(N=C=NC2CCCCC2)CCCCC1.[NH2:22][C:23]1[CH:24]=[CH:25][C:26]([Cl:29])=[N:27][CH:28]=1>O1CCCC1>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([NH:22][C:4](=[O:6])[CH2:3][C:1]#[N:2])=[CH:28][N:27]=1

Participants

5

Reactant 3

HCID 9740Cyanoacetic acidHCID 10868DicyclohexylcarbodiimideHCID 793055-Amino-2-chloropyridine

Product 1

HCID 10607908HCID 10607908, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.95 g (70.0 mmol) of cyanoacetic acid and 14.44 g (70.0 mmol) of dicyclohexylcarbodiimide were added to a stirred solution of 9.00 g (70.0 mmol) of 5-amino-2-chloropyridine in 150 ml of anhydrous tetrahydrofuran at 0° C. The reaction was monitored by thin layer chromatography and when complete, the reaction mixture was filtered and the filtrate was evaporated to dryness. The resulting solid was triturated with anhydrous dichloromethane, filtered and dried in vacuo to obtain 10.5 g of N-(2-chloropyrid-5-yl)-2-cyanoacetamide (77% yield).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customthe filtrate was evaporated to dryness
  3. customThe resulting solid was triturated with anhydrous dichloromethane
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-08e915aa9f9b485685a75b3157ae3b3b
Source dataset
uspto-grants-1994_09
Patent number
US05346912

Reaction notes

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