1-Diethoxyphosphorylpropan-2-one → HCID 59684847, compound

HRID 421799Notes

Reaction equation

HRID 421799 reaction equation
O=[C:2]([CH3:12])[CH2:3][P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7].[C:13]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)#[N:14].[F:23][C:24]([F:36])([F:35])[C:25]1[CH:26]=[C:27]([NH:31][C:32]([NH2:34])=[O:33])[CH:28]=[CH:29][CH:30]=1>O1CCCC1>[C:13]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]2[C:3]([P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])=[C:2]([CH3:12])[N:31]([C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([C:24]([F:35])([F:36])[F:23])[CH:26]=3)[C:32](=[O:33])[NH:34]2)=[CH:17][CH:16]=1)#[N:14]

Participants

5

Reactant 3

HCID 140281-Diethoxyphosphorylpropan-2-oneHCID 25712(3-Trifluoromethylphenyl)ureaHCID 660424-Cyanobenzaldehyde

Product 1

HCID 59684847HCID 59684847, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of diethyl (2-oxopropyl)phosphonate (250 mg, 1.29 mmol), 4-cyanobenzaldehyde (168.84 mg, 1.29 mmol), N-[3-(trifluoromethyl)phenyl]urea (263 mg, 1.29 mmol) and polyphosphoric acid ethyl ester (0.70 g) in tetrahydrofuran (5 ml) is refluxed overnight with stirring. The reaction solution is purified directly by preparative HPLC (RP18 column; eluent: acetonitrile/water 10:90→90:10). The fractions containing product are concentrated in vacuo and re-purified by flash chromatography on silica gel 60 with dichloromethane/methanol as eluent.

Workup

  1. customThe reaction solution is purified directly by preparative HPLC (RP18 column; eluent: acetonitrile/water 10:90→90:10)
  2. additionThe fractions containing product
  3. concentrationare concentrated in vacuo
  4. customre-purified by flash chromatography on silica gel 60 with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-b840854984ea4689811308eac39eb028
Source dataset
uspto-grants-2012_01
Patent number
US08101615B2

Reaction notes

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