Diethyl Ether → HCID 178522917, compound

HRID 2289895Notes

Reaction equation

HRID 2289895 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:10]1(=[O:24])OC(OC(CC)(CC)C)[O:14][C:12](=O)[CH2:11]1.[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1.[CH2:34](OCC)C>>[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH:31][C:10]([C:11]2[CH:34]=[N:4][C:3]3[C:5]([C:12]=2[OH:14])=[CH:6][C:7]([I:9])=[CH:8][C:2]=3[F:1])=[O:24])=[CH:28][CH:27]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 660364-ChlorobenzylamineHCID 1856942-Fluoro-4-iodoanilineHCID 131717023Diethylethoxymethylene malonate

Product 1

HCID 178522917HCID 178522917, compound

Conditions

Temperature
130 °C

Procedure

A mixture of 11.85 g of 2-fluoro-4-iodoaniline and 10.81 g of diethylethoxymethylene malonate is heated to 130° C. in a flask equipped with a Dean-Stark trap to collect formed ethanol. The mixture is then cooled to 75° C. and diluted with hexanes. The resulting solid is collected and dried. The solid is then dissolved in 60 mL diphenyl ether and heated to 250° C. for 3 h in a flask equipped with a Dean-Stark trap to collect the ethanol. The solution is allowed to cool to room temperature and the resulting solid is collected and dried to yield 11.73 g. This material(0.55 g) and 3 mL of 4-chlorobenzylamine are heated at 180° C. for 1 h. The reaction is cooled and poured into 75 mL diethyl ether. The resulting solid is filtered and recrystallized from ethyl acetate/hexanes to give the title compound as an off-white solid (0.45 g).

Workup

  1. customequipped with a Dean-Stark trap
  2. customto collect
  3. customformed ethanol
  4. temperatureThe mixture is then cooled to 75° C.
  5. customThe resulting solid is collected
  6. customdried
  7. dissolutionThe solid is then dissolved in 60 mL diphenyl ether
  8. temperatureheated to 250° C. for 3 h in a flask
  9. customequipped with a Dean-Stark trap
  10. customto collect the ethanol
  11. temperatureto cool to room temperature
  12. customthe resulting solid is collected
  13. customdried
  14. customto yield 11.73 g
  15. temperatureThe reaction is cooled
  16. filtrationThe resulting solid is filtered
  17. customrecrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-14677d8d875c486099f10fff928becf6
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

Loading…