Triethyl Phosphate → HCID 58133696, compound

HRID 707602Notes

Reaction equation

HRID 707602 reaction equation
P(OCC)(OCC)(OCC)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH:26][CH2:27][CH2:28][S:29]([C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[CH:40]=O)[C:35]#[N:36])(=[O:31])=[O:30].[F:42][C:43]([F:55])([F:54])[C:44]1[CH:45]=[C:46]([NH:50][C:51]([NH2:53])=[O:52])[CH:47]=[CH:48][CH:49]=1.[C:56]([O:62][CH2:63][CH:64]=[CH2:65])(=[O:61])[CH2:57][C:58]([CH3:60])=O>CC(OC)(C)C>[C:35]([C:34]1[CH:37]=[CH:38][C:39]([CH:40]2[C:57]([C:56]([O:62][CH2:63][CH:64]=[CH2:65])=[O:61])=[C:58]([CH3:60])[N:50]([C:46]3[CH:47]=[CH:48][CH:49]=[C:44]([C:43]([F:54])([F:55])[F:42])[CH:45]=3)[C:51](=[O:52])[NH:53]2)=[C:32]([S:29]([CH2:28][CH2:27][OH:26])(=[O:30])=[O:31])[CH:33]=1)#[N:36]

Participants

7

Reactant 5

HCID 6535Triethyl PhosphateHCID 14812Phosphorus oxide (P4O10)HCID 25712(3-Trifluoromethylphenyl)ureaHCID 70701Allyl acetoacetateHCID 58133725HCID 58133725, compound

Product 1

HCID 58133696HCID 58133696, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
90 °C

Procedure

The reaction was carried out under argon. Triethyl phosphate (1.43 g, 7.9 mmol; 1.2 eq.) and diphosphorus pentoxide (0.745 g; 0.8 eq.) were stirred at 40° C. overnight. The mixture was then diluted with MTBE (35 ml), and 3-[(2-hydroxyethyl)sulfonyl]-4-formylbenzonitrile (1.57 g, 6.6 mmol), 1-[3-(trifluoromethyl)phenyl]urea (1.34 g, 6.6 mmol) and allyl acetoacetate (1.4 g, 9.84 mmol; 1.5 eq.) were added. The mixture was stirred under reflux for 2 h. The reaction mixture was then concentrated by distillative removal of MTBE and subsequently heated at 90° C. for a further 5 h. For work-up, residual solvent was removed under reduced pressure and the residue was taken up in ethyl acetate (250 ml). The organic phase was washed with saturated sodium chloride solution (3×50 ml), dried over solid sodium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to flash chromatography on silica gel (mobile phase: cyclohexane→cyclohexane/ethyl acetate 2:3). The title compound was obtained as a colorless solid (1.22 g, 23% of theory).

Workup

  1. additionwere added
  2. temperatureunder reflux for 2 h
  3. concentrationThe reaction mixture was then concentrated by distillative removal of MTBE
  4. customFor work-up, residual solvent was removed under reduced pressure
  5. washThe organic phase was washed with saturated sodium chloride solution (3×50 ml)
  6. dry with materialdried over solid sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-91cb3f346a314f568d788d20e1253f3e
Source dataset
uspto-grants-2015_11
Patent number
US09174997B2

Reaction notes

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