Phosphorus oxychloride → HCID 10631964, compound

HRID 849984Notes

Reaction equation

HRID 849984 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([C:8]1[C:9](O)=[C:10]([N+:15]([O-:17])=[O:16])[C:11](=[O:14])[NH:12][CH:13]=1)[CH3:7]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C>[Cl:3][C:9]1[C:8]([CH2:6][CH3:7])=[CH:13][NH:12][C:11](=[O:14])[C:10]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 54707526HCID 54707526, compound

Product 1

HCID 10631964HCID 10631964, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

Phosphorus oxychloride (6.7 ml, 39.1 mmoles) was added to a solution of compound 5b (3.00 g, 16.3 mmoles) and benzyltriethylammonium chloride (14.90 g, 65.2 mmoles) in acetonitrile (60 ml). The mixture obtained was agitated at 40° C. for 30 minutes and heated under reflux for 1 hour. After evaporation of the solvent, 60 ml of water was added and the mixture agitated at ambient temperature for 3 hours. The yellow precipitate was collected, washed with cyclohexane (3×6 ml) and dried to give compound 6b (2.4 g, 74%) in the form of pale yellow crystals: NMR-1H (DMSO-d6) δ 13.19 (1H, s, NH-1), 7.73 (1H, s, H-6), 2.56 (2H, q, L=7.5 Hz, CH2CH3), 1.16 (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, 60 ml of water
  5. additionwas added
  6. stirringthe mixture agitated at ambient temperature for 3 hours
  7. customThe yellow precipitate was collected
  8. washwashed with cyclohexane (3×6 ml)
  9. customdried

Sources & evidence

ORD record
ord-03dd618ecc2c4c7188279e194d8633f8
Source dataset
uspto-grants-2000_01
Patent number
US06015820

Reaction notes

Loading…