Cyanoacetic acid → HCID 24694331, compound

HRID 1593759Notes

Reaction equation

HRID 1593759 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[NH2:6].[C:14]([CH2:16][C:17](O)=[O:18])#[N:15].C(N=C=NC(C)C)(C)C>O1CCCC1>[C:14]([CH2:16][C:17]([NH:6][C:5]1[CH:7]=[C:8]([O:12][CH3:13])[C:9]([O:10][CH3:11])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:18])#[N:15]

Participants

5

Reactant 3

HCID 9740Cyanoacetic acidHCID 12734DiisopropylcarbodiimideHCID 322853,4,5-Trimethoxyaniline

Product 1

HCID 24694331HCID 24694331, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4,5-Trimethoxyaniline (10.00 g, 54.6 mmol) and cyanoacetic acid (4.78 g, 56.19 mmol) were mixed in 100 mL of tetrahydrofuran and heated to reflux. To the resultant solution 1,3-diisopropylcarbodiimide (8.8 mL, 56.29 mmol) was added dropwise. The mixture was cooled in an ice-bath and the solid was collected by filtration washing with tetrahydrofuran. The filtrate was slowly poured into water and stirred for 30 minutes. The white solid was collected by filtration, washed with water and dried to give 2.58 g of 2-cyano-N-(3,4,5-trimethoxyphenyl)acetamide as a white solid, mp 146-147° C.; 1H NMR (400 MHz, DMSO-d6) δ 3.61 (s, 3H), 3.74 (s, 6H), 3.86 (s, 2H), 6.90 (s, 2H), 10.23 (s, 1H); MS (ES) m/z251.1 (M+H)+

Workup

  1. temperatureheated to reflux
  2. temperatureThe mixture was cooled in an ice-bath
  3. filtrationthe solid was collected by filtration
  4. washwashing with tetrahydrofuran
  5. additionThe filtrate was slowly poured into water
  6. filtrationThe white solid was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-779d3cb8fcec4f538fc4d28b218d25e6
Source dataset
uspto-grants-2007_11
Patent number
US07297795B2

Reaction notes

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