Cyanoacetic acid → HCID 2799775, compound

HRID 566252Notes

Reaction equation

HRID 566252 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[NH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([CH2:3][C:4]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:6])#[N:2]

Participants

6

Reactant 4

HCID 9740Cyanoacetic acidHCID 195092-PyridinemethanamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 2799775HCID 2799775, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyanoacetic acid (8.51 g) was dissolved in dichloromethane (400 ml). To the solution was added 2-aminomethylpyridine (10.81 g). The mixture was stirred for a while, to which was then added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (19.17 g). The mixture was stirred for 15 minutes at 25° C. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate (200 ml). The mixture was shaken and left standing. The.aqueous layer was subjected to extraction with ethyl acetate (200 ml) three times. The organic layers were combined and dried over anhydrous magnesium sulfate, followed by concentration to afford the title compound (15.51 g).

Workup

  1. stirringThe mixture was stirred for 15 minutes at 25° C
  2. stirringThe mixture was shaken
  3. waitleft standing
  4. extractionThe.aqueous layer was subjected to extraction with ethyl acetate (200 ml) three times
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-b94eb658116f456090fdb6f236f27fa3
Source dataset
uspto-grants-2001_01
Patent number
US06174877B1

Reaction notes

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