Cyanoacetic acid → 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide

HRID 1593758Notes

Reaction equation

HRID 1593758 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][CH3:11])=[CH:5][C:3]=1[NH2:4].[C:12]([CH2:14][C:15](O)=[O:16])#[N:13].C(N=C=NC(C)C)(C)C>O1CCCC1>[C:12]([CH2:14][C:15]([NH:4][C:3]1[CH:5]=[C:6]([O:10][CH3:11])[C:7]([Cl:9])=[CH:8][C:2]=1[Cl:1])=[O:16])#[N:13]

Participants

5

Reactant 3

HCID 9740Cyanoacetic acidHCID 12734DiisopropylcarbodiimideHCID 14766362,4-Dichloro-5-methoxyaniline

Product 1

HCID 160991782-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamideYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
15 °C

Procedure

2,4-Dichloro-5-methoxyaniline (5.00 g, 26 mmol) and cyanoacetic acid (2.28 g, 26.8 mmol) were mixed in 50 mL of tetrahydrofuran until a solution formed. This solution was heated to reflux and 1,3-diisopropylcarbodiimide (4.2 mL, 26.8 mmol) was added dropwise. After 30 minutes the mixture was cooled to ˜15° C. in an ice-bath. The solid was collected by filtration and washed 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 was then dissolved in 500 mL of ethyl acetate. The solution was dried over sodium sulfate and concentrated in vacuo to give 5.9 g (88%) of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide as a white solid, mp 180-181° C.; 1H NMR (400 MHz, DMSO-d6) δ 3.84 (s, 3H), 4.02 (s, 2H), 7.58 (s, 1 H), 7.66 (s, 1 H), 10.00 (s, 1 H); MS (ES) m/z257.0, 259.0 (M−H)−

Workup

  1. customformed
  2. temperatureThis solution was heated
  3. temperatureto reflux
  4. filtrationThe solid was collected by filtration
  5. washwashed with tetrahydrofuran
  6. additionThe filtrate was slowly poured into water
  7. filtrationThe white solid was collected by filtration
  8. washwashed with water
  9. dissolutionwas then dissolved in 500 mL of ethyl acetate
  10. dry with materialThe solution was dried over sodium sulfate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b024c98b5b13422cb82bee4b7cd19512
Source dataset
uspto-grants-2007_11
Patent number
US07297795B2

Reaction notes

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