Phosphorus oxychloride → HCID 22643320, compound

HRID 2414821Notes

Reaction equation

HRID 2414821 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][NH:17][C:18](=O)[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)=[CH:11][C:10]=1[O:29][CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl.[BH4-].[Na+]>CC#N.CO>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]2[C:12]([CH2:15][CH2:16][NH:17][CH:18]2[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)=[CH:11][C:10]=1[O:29][CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 4311764Sodium borohydrideHCID 69763755HCID 69763755, compound

Product 1

HCID 22643320HCID 22643320, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of N-[2-(4-benzyloxy-3-methoxy-phenyl)-vinyl]-2-(3,4-dichloro-phenyl)-acetamide (13.3 g, 30 mmol) in CH3CN (100 mL) at rt is added dropwise phosphoroxychloride (8.1 mL, 13.5 g, 88 mmol). The resulting white suspension is heated to reflux, and the resulting yellow solution is heated at reflux for 3 h. The dark yellow solution is allowed to cool and is evaporated to a yellow oil. The oil is taken up in MeOH (100 mL) and evaporated to yield an orange solid. The material is redissolved in MeOH (100 mL) and the solution is cooled to 0° C. NaBH4 (3.61 g, 95 mmol) is added in portions with gas evolution and a strong exotherm. The resulting white suspension is stirred at rt for 16 h. The reaction mixture is partitioned between EtOAc (200 mL) and water (200 mL), and the aqueous phase is extracted with EtOAc (3×200 mL). The combined organic phase is washed with water and brine, and evaporated to provide the title compound as a faint yellow oil which is used without further purification.

Workup

  1. temperatureThe resulting white suspension is heated
  2. temperatureto reflux
  3. temperaturethe resulting yellow solution is heated
  4. temperatureat reflux for 3 h
  5. temperatureto cool
  6. customis evaporated to a yellow oil
  7. customevaporated
  8. customto yield an orange solid
  9. customThe reaction mixture is partitioned between EtOAc (200 mL) and water (200 mL)
  10. extractionthe aqueous phase is extracted with EtOAc (3×200 mL)
  11. washThe combined organic phase is washed with water and brine
  12. customevaporated

Sources & evidence

ORD record
ord-3e1135398647407da370bb3e21810d9d
Source dataset
uspto-grants-2004_11
Patent number
US06815451B2

Reaction notes

Loading…