Phosphorus pentachloride → HCID 87345098, compound

HRID 925029Notes

Reaction equation

HRID 925029 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[C:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18](=O)[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)([CH3:10])([CH3:9])[CH3:8]>C1C=CC=CC=1>[C:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]=[C:18]([Cl:2])[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 893019HCID 893019, compound

Product 1

HCID 87345098HCID 87345098, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Phosphorus pentachloride (6.88 g, 33 mmol) was dissolved in 50 mL of benzene. Under a gentle argon purge, N-(2-tert-butylphenyl)-4-methylbenzamide (Amide II) (8.02 g, 30 mmol) was added slowly with stiffing at room temperature. The yellow solution was refluxed for 2 hours. Benzene was removed in vacuo, yielding a yellow solid (8.22 g, 96%). 1H NMR (400 MHz, C6D6): 8.17 (d, 2H), 7.38 (d, 1H), 7.11 (t, 1H), 7.06 (t, 1H), 6.90 (d, 2H), 6.85 (d, 1H), 1.98 (s, 3H), 1.42 (s, 9H).

Workup

  1. customUnder a gentle argon purge
  2. customwith stiffing at room temperature
  3. temperatureThe yellow solution was refluxed for 2 hours
  4. customBenzene was removed in vacuo

Sources & evidence

ORD record
ord-269eae3ca5ba45c0aa243dd6c24fd33a
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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