N,N-Diethylaniline → HCID 67926704, compound

HRID 344608Notes

Reaction equation

HRID 344608 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:13]2[C:21](=O)[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[NH:14]2)([F:12])[CH:6]2[C:10]=1[O:9][CH:8]([CH3:11])[CH2:7]2.P(Cl)(Cl)([Cl:25])=O.C(N(CC)C1C=CC=CC=1)C>C(OCC)(=O)C>[Cl:25][C:21]1[N:13]([C:5]2([F:12])[CH:6]3[CH2:7][CH:8]([CH3:11])[O:9][C:10]3=[C:2]([Cl:1])[CH:3]=[CH:4]2)[N:14]=[C:15]2[C:20]=1[CH2:19][CH2:18][CH2:17][CH2:16]2

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 67926702HCID 67926702, compound

Product 1

HCID 67926704HCID 67926704, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.25 g of 39C was mixed with 0.14 g of phosphorous oxychloride and 0.15 g of N,N-diethylaniline and heated under nitrogen at 135°-140° C. for three hours, cooled, and diluted with ethyl acetate. The organic phase was washed with water, 10% hydrochloric acid, saturated sodium bicarbonate solution, brine, dried (MgSO4) and stripped of solvent. The residue was purified by flash chromatography on silica gel, using a 1:4 v:v mixture of ether and hexane as eluent to afford the title compound as a yellow glass.

Workup

  1. temperatureheated under nitrogen at 135°-140° C. for three hours
  2. temperaturecooled
  3. washThe organic phase was washed with water, 10% hydrochloric acid, saturated sodium bicarbonate solution, brine
  4. dry with materialdried (MgSO4)
  5. customThe residue was purified by flash chromatography on silica gel
  6. additionv mixture of ether and hexane as eluent

Sources & evidence

ORD record
ord-5a32b1b272414f7ebf398c03b8494b94
Source dataset
uspto-grants-1991_10
Patent number
US05053071

Reaction notes

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