Phosphorus oxychloride → HCID 18172446, compound

HRID 397037Notes

Reaction equation

HRID 397037 reaction equation
[CH2:1]([O:8][C:9]1[CH:25]=[CH:24][C:12]([C:13]([NH:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl>>[CH2:1]([O:8][C:9]1[CH:25]=[CH:24][C:12]([C:13]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][N:15]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 4958359HCID 4958359, compound

Product 1

HCID 18172446HCID 18172446, compoundYield 28.7%

Procedure

A solution of 4-benzyloxy-N-phenethylbenzamide (1.000 g, 3.0 mmol) in POCl3 (10 ml, 107.3 mmol) was refluxed under N2 for 18 hr, then the cooled reaction mixture was slowly added to ice-water (50 ml) with stirring. The resulting mixture was extracted with EtOAc (4×20 ml), then the remaining aqueous layer was basified to pH 10 with concentrated ammonia (80 ml). This was extracted with EtOAc (3×50 ml), then the combined extracts were dried over MgSO4 and concentrated in vacuo to give 0.270 g of yellow solid. Purification by flash chromatography, eluting with hexane:EtOAc (6:4) gave 0.151 g (16% yield) of yellow solid.

Workup

  1. customthe cooled reaction mixture
  2. extractionThe resulting mixture was extracted with EtOAc (4×20 ml)
  3. extractionThis was extracted with EtOAc (3×50 ml)
  4. dry with materialthe combined extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3bab8bbe817b4753ae9a798e328dd732
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

Loading…