Hexane → HCID 18172437, compound

HRID 397031Notes

Reaction equation

HRID 397031 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[CH2:7]([O:14][C:15]1[CH:33]=[CH:32][C:18]([C:19]([NH:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)=O)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCCCCC>ClCCCl>[ClH:2].[CH2:7]([O:14][C:15]1[CH:33]=[CH:32][C:18]([C:19]2[C:29]3[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=3)[CH2:23][CH2:22][N:21]=2)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 24819Phosphorus pentachlorideHCID 18172425HCID 18172425, compound

Product 1

HCID 18172437HCID 18172437, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

Phosphorus pentachloride (58.557 g, 281.2 mmol) was added in portions to a solution of 4-benzyloxy-N-[2-(3-methoxyphenyl)ethyl]benzamide (59.775 g, 165.4 mmol) in 1,2-dichloroethane (500 ml) at 0° C. under N2. The resulting reaction was stirred at 0° C. for 30 min, then refluxed for 18 hr. After cooling to rt, hexane (1200 ml) was added and the resulting suspension was cooled to 0° C. The solvent was decanted off from the oil that separated and the remaining oil was dried in vacuo to give 54.56 g (87% yield) of orange residue.

Workup

  1. customThe resulting reaction
  2. temperaturerefluxed for 18 hr
  3. temperatureAfter cooling to rt
  4. temperaturethe resulting suspension was cooled to 0° C
  5. customThe solvent was decanted off from the oil
  6. customthat separated
  7. customthe remaining oil was dried in vacuo

Sources & evidence

ORD record
ord-d2c2896534fc46a78a9a1086e83c46f3
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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