Phosphorus oxychloride → HCID 24958350, compound

HRID 1258425Notes

Reaction equation

HRID 1258425 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[O:20][C:14]4[NH:15][C:16](=O)[N:17]=[CH:18][C:13]=4[C:12]=3[C:21]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.P(Cl)(Cl)([Cl:35])=O>>[Cl:35][C:16]1[N:17]=[CH:18][C:13]2[C:12]([C:21]3[CH:22]=[C:23]([O:31][CH3:32])[C:24]([O:29][CH3:30])=[C:25]([O:27][CH3:28])[CH:26]=3)=[C:11]([C:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[N:2]([CH3:1])[CH:3]=[CH:4]4)[O:20][C:14]=2[N:15]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 24821058HCID 24821058, compound

Product 1

HCID 24958350HCID 24958350, compound

Procedure

The product of example 4 (200 mg, 0.46 mmol) was heated in freshly distilled P(O)Cl3 (10 ml) to 90° C. for 3 hours and then solvents were removed under vacuum. The residue was dissolved in CH2Cl2 and washed with aqueous NaHCO3 and evaporated. The residue was purified by silica gel column chromatography using increasing gradient of CH2Cl2 in hexane to pure CH2Cl2. Yield (40%); 1H NMR (300 MHz, CDCl3) δ: 3.77 (s, 6H, 2×OMe), 3.79 (s, 3H, OMe), 3.94 (s, 3H, OMe), 6.49 (d, J=3.0 Hz, 1H), 6.71 (s, 2H), 7.08 (d, J=3.0 Hz, 1H), 7.27 (d, J=9.0 Hz, 1H), 7.53 (dd, J=9.0, 1.2 Hz, 1H), 8.05 (d, J=1.2 Hz, 1H), 8.72 (bs, 1H).

Workup

  1. customsolvents were removed under vacuum
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with aqueous NaHCO3
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography
  6. temperatureusing increasing gradient of CH2Cl2 in hexane to pure CH2Cl2
  7. customYield (40%)

Sources & evidence

ORD record
ord-24a16098c8f144008b0444269adee183
Source dataset
uspto-grants-2013_06
Patent number
US08466163B2

Reaction notes

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