Phosphorus oxychloride → HCID 86716489, compound

HRID 1747713Notes

Reaction equation

HRID 1747713 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16](=O)[NH:15][N:14]=1)=O.P(Cl)(Cl)([Cl:22])=O>S1(CCCC1)(=O)=O>[Cl:22][C:16]1[CH:17]=[CH:18][C:13]2[N:14]([C:9]([CH2:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[N:11][CH:12]=2)[N:15]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86716488HCID 86716488, compound

Product 1

HCID 86716489HCID 86716489, compound

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
100 °C

Procedure

65.00 g (248.79 mmol) of the compound obtained in Example 2A were initially charged in sulfolane (780 ml), 185.52 ml (1.990 mol) of phosphorus oxychloride were added and the mixture was then stirred at 100° C. for 3 h. Excess phosphorus oxychloride was then distilled off under high vacuum, and the residue was taken up in ethyl acetate and added to a saturated aqueous sodium bicarbonate solution. The mixture was diluted with water and then extracted with ethyl acetate. The organic phases were combined, washed with water, dried and concentrated. The residue was purified by chromatography on silica gel (mobile phase:dichloromethane/methanol 20:1→5:1 (v/v)), then washed once more with water and purified once more by chromatography on silica gel (mobile phase:dichloromethane/methanol 100:1 v/v). This gave 23.6 g of the target compound (36% of theory).

Workup

  1. distillationExcess phosphorus oxychloride was then distilled off under high vacuum
  2. additionadded to a saturated aqueous sodium bicarbonate solution
  3. additionThe mixture was diluted with water
  4. extractionextracted with ethyl acetate
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (mobile phase:dichloromethane/methanol 20:1→5:1 (v/v))
  9. washwashed once more with water
  10. custompurified once more by chromatography on silica gel (mobile phase:dichloromethane/methanol 100:1 v/v)

Sources & evidence

ORD record
ord-b5ab01997225414a80230a06e5ebfdee
Source dataset
uspto-grants-2015_10
Patent number
US09150580B2

Reaction notes

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