Cyanoacetic acid → n-(4-chlorobenzyl)-2-cyanoacetamide

HRID 1624876Notes

Reaction equation

HRID 1624876 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[C:10]([CH2:12][C:13](O)=[O:14])#[N:11].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:13](=[O:14])[CH2:12][C:10]#[N:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 9740Cyanoacetic acidHCID 660364-ChlorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 690673n-(4-chlorobenzyl)-2-cyanoacetamideYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

According to the Scheme 1 Step 1: A mixture of 4-chlorobenzylamine (10.0 g, 71 mmol), cyanoacetic acid (6.13 g, 72 mmol), HOBt (11 g, 72 mmol), EDCI.HCl (20 g, 106 mmol) in 100 mL of dioxane was stirred for 3 h at room temperature. The solvent was removed under vacuum and 300 mL of DCM was added. The organic layer was successively washed with 2×100 mL of water, 2×50 mL of a solution 1N of NaOH, 4×100 mL of water until neutral pH. The organic layer was dried over Na2SO4, filtered and concentrated to afford N-(4-chlorobenzyl)-2-cyanoacetamide 1(A) (13.12 g, 89%) as a brown solid.

Workup

  1. customThe solvent was removed under vacuum and 300 mL of DCM
  2. additionwas added
  3. washThe organic layer was successively washed with 2×100 mL of water, 2×50 mL of a solution 1N of NaOH, 4×100 mL of water until neutral pH
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0725fff2b58f4b3f98b9f311e491f90d
Source dataset
uspto-grants-2014_07
Patent number
US08779129B2

Reaction notes

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