Ethyl orthoformate → 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-[(4-ethoxy-3-iodophenyl)amino]prop-2-enamide

HRID 1593773Notes

Reaction equation

HRID 1593773 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].[CH2:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][C:21]=1[I:27])[CH3:18].[CH2:28](OC(OCC)OCC)C>C(O)(C)C>[C:1]([C:3](=[CH:28][NH:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][CH2:17][CH3:18])=[C:21]([I:27])[CH:22]=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]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 160991782-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamideHCID 57419509HCID 57419509, compound

Product 1

HCID 692583872-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-[(4-ethoxy-3-iodophenyl)amino]prop-2-enamideYield 54%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (5.44 g, 21.0 mmol) in 350 mL of iso-propanol, under N2, was added (4-ethoxy-3-iodophenyl)amine (5.0 g, 19.30 mmol). This mixture was heated to reflux and triethylorthoformate (8.53 mL, 51.30 mmol) was added dropwise and the reaction mixture was heated at reflux overnight. The mixture was allowed to cool to room temperature and the yellow solid was collected by filtration, washed with iso-propanol, and dried overnight at ˜40° C. under reduced pressure to give 5.46 g (54%) of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-[(4-ethoxy-3-iodophenyl)amino]prop-2-enamide as a yellow solid, mp >245° C.; MS (EI) m/z 531.01 (M)+

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux overnight
  5. filtrationthe yellow solid was collected by filtration
  6. washwashed with iso-propanol
  7. customdried overnight at ˜40° C. under reduced pressure

Sources & evidence

ORD record
ord-251e9f3beccb44f5a7ec768da4718a34
Source dataset
uspto-grants-2007_11
Patent number
US07297795B2

Reaction notes

Loading…