Phosphorus oxychloride → HCID 57687362, compound

HRID 559067Notes

Reaction equation

HRID 559067 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](O)=[CH:10][C:9](=[O:13])[N:8]([CH3:14])[C:7]=1[NH:15][CH3:16])=[O:5])[CH3:2].O=P(Cl)(Cl)[Cl:19]>CN(C)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:11]([Cl:19])=[CH:10][C:9](=[O:13])[N:8]([CH3:14])[C:7]=1[NH:15][CH3:16])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 57687371HCID 57687371, compound

Product 1

HCID 57687362HCID 57687362, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 949N,N-DimethylanilineCatalyst

Procedure

Dimethylaniline (0.770 mL, 0.61 mmol) was added to a stirring solution of example 31b (15 g, 66.1 mmol) in POCl3 (36 mL, 397 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 21 h. The reaction was concentrated in vacuo, poured onto ice, and the resulting precipitate was collected by filtration to give 14 g (87%) of clean desired product as a beige solid. The filtrate was extracted with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated under reduced pressure to give an additional 2 g (12%) of clean desired product. 1H NMR (400 MHz, DMSO-d6): δ 6.99 (q, 1H, J=4.8 Hz), 5.80 (s, 1H), 4.23 (q, 2H, J=7.2 Hz), 3.32 (s, 3H), 2.76 (d, 3H, J=4.8 Hz), 1.27 (t, 3H, J=7.2 Hz). MS (ES) [m+H] calc'd for C10H13ClN2O3, 245; found 245.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionpoured onto ice
  3. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-7b779d8793054247a02a42f847234180
Source dataset
uspto-grants-2011_11
Patent number
US08063066B2

Reaction notes

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