Diethyl chlorophosphate → 4-(2,5-Dimethoxycinnamoylamino)-2,6-dimethylphenol

HRID 728344Notes

Reaction equation

HRID 728344 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:4]=1[CH:5]=[CH:6][C:7]([OH:9])=O.C(OP(Cl)(=O)OCC)C.[NH2:25][C:26]1[CH:31]=[C:30]([CH3:32])[C:29]([OH:33])=[C:28]([CH3:34])[CH:27]=1.C(=O)([O-])O.[Na+]>C(#N)C.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:4]=1[CH:5]=[CH:6][C:7]([NH:25][C:26]1[CH:31]=[C:30]([CH3:32])[C:29]([OH:33])=[C:28]([CH3:34])[CH:27]=1)=[O:9]

Participants

7

Reactant 4

HCID 13139Diethyl chlorophosphateHCID 826684-Amino-2,6-dimethylphenolHCID 1145783-(2,5-Dimethoxyphenyl)-2-propenoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 543033924-(2,5-Dimethoxycinnamoylamino)-2,6-dimethylphenolYield 71%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

Under ice-cooling, 4.16 g of 2,5-dimethoxycinnamic acid is dissolved in 50 ml of acetonitrile, and to the resultant solution are added 3.03 g of triethylamine, then 4.13 g of diethylphosphorochloridate. After the mixture is stirred for one hour, 2.74 g of 4-amino-2,6-dimethylphenol is added and the reaction mixture is stirred at room temperature. After completion of the reaction, ice chips are added, and then 5 % aqueous sodium hydrogen carbonate solution is added. The crystals precipitated are collected by filtration, and washed with isopropyl ether. The crystals obtained are recrystallized form ethyl acetate to give 4.64 g of 4-(2,5-dimethoxycinnamoylamino)-2,6-dimethylphenol as white crystals.

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe reaction mixture is stirred at room temperature
  3. customAfter completion of the reaction, ice chips
  4. additionare added
  5. customThe crystals precipitated
  6. filtrationare collected by filtration
  7. washwashed with isopropyl ether
  8. customThe crystals obtained
  9. customare recrystallized form ethyl acetate

Sources & evidence

ORD record
ord-c572ecf11ad0400c90d5ef06a4ec4d97
Source dataset
uspto-grants-1991_09
Patent number
US05047555

Reaction notes

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