Diethyl Ether → HCID 18172383, compound

HRID 397041Notes

Reaction equation

HRID 397041 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[I:7][C:8]1[CH:26]=[CH:25][C:11]([C:12]([NH:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)=O)=[CH:10][CH:9]=1.CCCCCC.CCOCC>C(Cl)(Cl)Cl>[ClH:2].[I:7][C:8]1[CH:26]=[CH:25][C:11]([C:12]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH3:24])=[CH:20][CH:21]=3)[CH2:16][CH2:15][N:14]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 24819Phosphorus pentachlorideHCID 18172471HCID 18172471, compound

Product 1

HCID 18172383HCID 18172383, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Phosphorus pentachloride (11 g, 52.8 mmol) was added in portions to a solution of 4-iodo-N-[2-(3-methoxyphenyl)-ethyl]benzamide (10.1 g, 26 mmol) in CHCl3 (60 ml) at 0° C. under N2. The resulting reaction was stirred at 0° C. for 10 min, then warmed to rt and stirred at rt for 18 hr. After cooling to 0° C., hexane (500 ml) was added and the resulting suspension was allowed to settle. The solvent was decanted off from the oil that separated and the remaining oil was triturated with EtOH (20 ml) to give a white solid. Et2O (200 ml) was added, the resulting suspension was stirred for 1 hr, the solid was collected and dried in vacuo to give 7.5 g (72% yield) of white solid.

Workup

  1. customThe resulting reaction
  2. temperaturewarmed to rt
  3. stirringstirred at rt for 18 hr
  4. temperatureAfter cooling to 0° C.
  5. customThe solvent was decanted off from the oil
  6. customthat separated
  7. customthe remaining oil was triturated with EtOH (20 ml)
  8. customto give a white solid
  9. stirringthe resulting suspension was stirred for 1 hr
  10. customthe solid was collected
  11. customdried in vacuo

Sources & evidence

ORD record
ord-4fb59b7ebc724059a8b715d7afbc05c4
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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