Phosphorus pentachloride → HCID 87345395, compound

HRID 925028Notes

Reaction equation

HRID 925028 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[CH2:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=O)[CH3:17])[CH3:8]>C1C=CC=CC=1>[Cl:2][C:16](=[N:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:7][CH3:8])[CH3:17]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 36332O-Ethylacetanilide

Product 1

HCID 87345395HCID 87345395, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Phosphorus pentachloride (8.97 g, 43 mmol) was dissolved in 100 mL of benzene. Under a gentle argon purge, N-(2-ethylphenyl)acetamide (Amide I) (6.52 g, 40 mmol) was added slowly with stirring at room temperature. The yellow solution was refluxed for 2 hours. Benzene was removed in vacuo, yielding a brown oil. The oil was distilled under reduced pressure (45-50° C., 0.10 Torr) affording 6.08 g (84%) of a clear oil. 1H NMR (400 MHz, C6D6): 7.07 (t, 2H), 6.99 (t, 1H), 6.80 (d, 1H), 2.50 (q, 2H), 2.08 (s, 3H), 1.11 (t, 3H).

Workup

  1. customUnder a gentle argon purge
  2. temperatureThe yellow solution was refluxed for 2 hours
  3. customBenzene was removed in vacuo
  4. customyielding a brown oil
  5. distillationThe oil was distilled under reduced pressure (45-50° C., 0.10 Torr)

Sources & evidence

ORD record
ord-01863a4a535a4201a7fd7df23651b27c
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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