Phosphorus oxychloride → HCID 10846413, compound

HRID 849985Notes

Reaction equation

HRID 849985 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][CH3:9])=[CH:6][NH:5][C:4](=[O:10])[C:3]=1[N+:11]([O-:13])=[O:12].P(Cl)(Cl)(Cl)=O.[CH2:19](C1C(O)=C([N+]([O-])=O)C(=O)NC=1C)C>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C>[Cl:1][C:2]1[C:7]([CH2:8][CH3:9])=[C:6]([CH3:19])[NH:5][C:4](=[O:10])[C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 10631964HCID 10631964, compoundHCID 54687507HCID 54687507, compound

Product 1

HCID 10846413HCID 10846413, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

As described for compound 6b in example 7, phosphorus oxychloride (8.3 ml, 88.8 mmoles) was added to a solution of compound 5c (4.00 g, 20.2 mmoles) and benzyltriethylammonium chloride (18.40 g, 80.8 mmoles) in acetonitrile (80 ml). The mixture obtained was agitated at 40° C. for 30 minutes and heated under reflux for 1 hour. After evaporation of the solvent, 150 ml of water was added and the mixture agitated at ambient temperature for 48 hours. The brown precipitate was collected, washed with cyclohexane (3×10 ml) and recrystallised in ethanol to give compound 6c (1.5 g, 34%) in the form of pale yellow crystals: NMR-1H (DMSO-d6) δ 12.98 (1H, s, NH-1), 2.58 (2H, q, L=7.5 Hz, CH2CH3), 2.38 (3H, s, CH3 -6), 1.08 (3H, t, J=7.5 Hz, CH2CH3 ).

Workup

  1. customThe mixture obtained
  2. temperatureheated
  3. temperatureunder reflux for 1 hour
  4. customAfter evaporation of the solvent, 150 ml of water
  5. additionwas added
  6. stirringthe mixture agitated at ambient temperature for 48 hours
  7. customThe brown precipitate was collected
  8. washwashed with cyclohexane (3×10 ml)
  9. customrecrystallised in ethanol

Sources & evidence

ORD record
ord-96b5e7a4863949a292cfb756be71dec8
Source dataset
uspto-grants-2000_01
Patent number
US06015820

Reaction notes

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