Triethyl Phosphate → HCID 58266260, compound

HRID 2039692Notes

Reaction equation

HRID 2039692 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH2:21])=[O:20])=[CH:14][C:13]=1[C:22]([F:25])([F:24])[F:23].[C:26]([O:32][CH2:33][CH3:34])(=[O:31])[CH2:27][C:28]([CH3:30])=O.P(OCC)(OCC)(OCC)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1COCC1>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH:1]2[C:27]([C:26]([O:32][CH2:33][CH3:34])=[O:31])=[C:28]([CH3:30])[N:18]([C:15]3[CH:16]=[CH:17][C:12]([F:11])=[C:13]([C:22]([F:23])([F:24])[F:25])[CH:14]=3)[C:19](=[O:20])[NH:21]2)=[CH:4][CH:5]=1)#[N:8]

Participants

7

Reactant 5

HCID 6535Triethyl PhosphateHCID 8868Ethyl AcetoacetateHCID 14812Phosphorus oxide (P4O10)HCID 660424-CyanobenzaldehydeHCID 58266265HCID 58266265, compound

Product 1

HCID 58266260HCID 58266260, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was carried out under argon. In succession, 4-formylbenzonitrile (656 mg, 5.0 mmol), 1-[4-fluoro-3-(trifluoromethyl)phenyl]urea (1.11 g, 5.0 mmol) and ethyl acetoacetate (651 mg, 5.0 mmol) were added 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 2:3). This gave 1.40 g (63% 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 2:3)

Sources & evidence

ORD record
ord-5f34a0f8d8b9492c85cb5dbabe8f661b
Source dataset
uspto-grants-2013_11
Patent number
US08580800B2

Reaction notes

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