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Ethyl orthoformate → 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{[3-iodo-4-(2-methoxyethoxy)phenyl]amino}acrylamide

HRID 1593774
Notes
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Reaction equation

HRID 1593774 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].[I:17][C:18]1[CH:19]=[C:20]([NH2:29])[CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH2:26][O:27][CH3:28].[CH2:30](OC(OCC)OCC)C>C(O)(C)C>[C:1]([C:3](=[CH:30][NH:29][C:20]1[CH:21]=[CH:22][C:23]([O:24][CH2:25][CH2:26][O:27][CH3:28])=[C:18]([I:17])[CH:19]=1)[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 31214Ethyl orthoformate2×HCID 160991782-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamideHCID 660942063-Iodo-4-(2-methoxyethoxy)aniline

Product 1

HCID 693123182-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{[3-iodo-4-(2-methoxyethoxy)phenyl]amino}acrylamideYield 78.9%

Reagents, catalysts & solvents 1

HCID 3776
Isopropanol
Solvent

Procedure

A suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (3.2 g, 12.4 mmol) and [3-iodo-4-(2-methoxyethoxy)phenyl]amine (4.0 g, 13.7 mmol) in 350 mL of iso-propanol was heated to reflux and triethylorthoformate (5.6 mL, 33.7 mmol) was added dropwise. The reaction mixture was heated at reflux for 3 hours. Additional triethylorthoformate (2.0 mL, 12.0 mmol) was added dropwise and the reaction mixture was heated at reflux overnight. The mixture was allowed to cool to room temperature and the solid was collected by filtration, washed with iso-propanol, diethyl ether, and ethyl acetate and then dried in vacuo to give 5.5 g of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{[3-iodo-4-(2-methoxyethoxy)phenyl]amino}acrylamide as a yellow solid, mp 209-210° C.; MS (ES) 560.0, 562.1 (M−H)−

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 3 hours
  5. temperaturethe reaction mixture was heated
  6. temperatureat reflux overnight
  7. filtrationthe solid was collected by filtration
  8. washwashed with iso-propanol, diethyl ether, and ethyl acetate
  9. customdried in vacuo

Sources & evidence

ORD record
ord-91a3f71283404d0bac78272c45df537c
Source dataset
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07297795B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes