Triethyl Phosphate → HCID 58266259, compound

HRID 2039690Notes

Reaction equation

HRID 2039690 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[C:11]([F:14])([F:13])[F:12])=O.[F:15][C:16]([F:28])([F:27])[C:17]1[CH:18]=[C:19]([NH:23][C:24]([NH2:26])=[O:25])[CH:20]=[CH:21][CH:22]=1.[C:29]([O:35][CH2:36][CH3:37])(=[O:34])[CH2:30][C:31]([CH3:33])=O.P(OCC)(OCC)(OCC)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1COCC1>[CH3:33][C:31]1[N:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:27])([F:28])[F:15])[CH:18]=2)[C:24](=[O:25])[NH:26][CH:1]([C:3]2[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=2[C:11]([F:14])([F:13])[F:12])[C:30]=1[C:29]([O:35][CH2:36][CH3:37])=[O:34]

Participants

7

Reactant 5

HCID 6535Triethyl PhosphateHCID 8868Ethyl AcetoacetateHCID 14812Phosphorus oxide (P4O10)HCID 25712(3-Trifluoromethylphenyl)ureaHCID 22118007HCID 22118007, compound

Product 1

HCID 58266259HCID 58266259, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was carried out under argon. 4-Formyl-3-(trifluoromethyl)benzonitrile (996 mg, 5.0 mmol; for the preparation cf. WO 98/37058), 1-[3-(trifluoromethyl)phenyl]urea (1.02 g, 5.0 mmol) and ethyl acetoacetate (651 mg, 5.0 mmol) were added successively to a solution of ethyl polyphosphate (2.0 g; prepared from triethyl phosphate and diphosphorus pentoxide analogously to the process in Example 18A) in THF (25 ml). The mixture was stirred under reflux for 19 h and then concentrated. Ethyl acetate (150 ml) was added to the residue, and the mixture was washed successively with water (50 ml), saturated sodium bicarbonate solution (50 ml) and saturated sodium chloride solution (50 ml). The organic phase was dried over sodium sulphate and concentrated. The residue was purified by silica gel chromatography (mobile phase: cyclohexane→cyclohexane/ethyl acetate 2:1). This gave 1.55 g (62% of theory) of the target product.

Workup

  1. temperatureunder reflux for 19 h
  2. concentrationconcentrated
  3. additionEthyl acetate (150 ml) was added to the residue
  4. washthe mixture was washed successively with water (50 ml), saturated sodium bicarbonate solution (50 ml) and saturated sodium chloride solution (50 ml)
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (mobile phase: cyclohexane→cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-a9e80b837f5d41f69a2ba28fd6632688
Source dataset
uspto-grants-2013_11
Patent number
US08580800B2

Reaction notes

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