Ethyl orthoformate → 3-(3-chloropropoxy)-4-methoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide

HRID 1593767Notes

Reaction equation

HRID 1593767 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=1[Cl:16])=[O:5])#[N:2].[Cl:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[NH2:25].[CH2:31](OC(OCC)OCC)C>C(O)(C)C>[Cl:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[NH:25][CH:31]=[C:3]([C:1]#[N:2])[C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=1[Cl:16])=[O:5]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 160991782-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamideHCID 693135373-(3-Chloropropoxy)-4-methoxyaniline

Product 1

HCID 693108673-(3-chloropropoxy)-4-methoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamideYield 44.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (738 mg, 2.84 mmol) in 100 mL of isopropanol was added 3-(3-chloropropoxy)-4-methoxyaniline (611 mg, 2.84 mmol). This mixture was heated to reflux and triethylorthoformate (3.0 mL, 18.0 mmol) was added dropwise. The reaction mixture was heated at reflux overnight. The mixture was filtered while still warm and the collected white solid was washed with isopropanol to give 610 mg of 3-(3-chloropropoxy)-4-methoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide, mp 185-192° C.; MS (ES) m/z 482.1, 484.2, 486.0 (M−H)−

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux overnight
  5. filtrationThe mixture was filtered
  6. temperaturewhile still warm
  7. washthe collected white solid was washed with isopropanol

Sources & evidence

ORD record
ord-3d228661e6544edaa7fdc2f0642c2626
Source dataset
uspto-grants-2007_11
Patent number
US07297795B2

Reaction notes

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