Phosphorus oxychloride → HCID 58149900, compound

HRID 2192465Notes

Reaction equation

HRID 2192465 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH:19]=[CH:20][N+:21]([O-])=[CH:22]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].P(Cl)(Cl)([Cl:30])=O>>[Cl:30][C:22]1[C:23]2[C:18](=[C:17]([C:14]3[N:13]=[C:12]([C:4]4[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[C:2]([Cl:1])[CH:3]=4)[O:16][N:15]=3)[CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:20][N:21]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66877400HCID 66877400, compound

Product 1

HCID 58149900HCID 58149900, compoundYield 92.2%

Conditions

Temperature
65 °C

Procedure

5-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)isoquinoline 2-oxide (D6; 1.18 g, 3.09 mmol) and phosphorus oxychloride (5.76 ml, 61.8 mmol) was stirred under an atmosphere of argon at room temperature for 4 hours. The mixture was then heated to 65° C. for 15 minutes, the phosphorus oxychloride evaporated under reduced pressure, and the residue, azeotroped with toluene and dried under vacuum overnight. The pale yellow solid residue was dissolved in dichloromethane (50 ml) and stirred with 2M NaOH (10 ml). The organic layer was separated, dried with MgSO4 and evaporated to dryness under reduced pressure to give a pale yellow solid (1.14 g) which was chromatographed over silica eluting with dichloromethane to give the title compound as a white solid (0.85 g).

Workup

  1. customthe phosphorus oxychloride evaporated under reduced pressure
  2. customthe residue, azeotroped with toluene
  3. customdried under vacuum overnight
  4. dissolutionThe pale yellow solid residue was dissolved in dichloromethane (50 ml)
  5. customThe organic layer was separated
  6. dry with materialdried with MgSO4
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d3dc7fff774a47ac85988e568ff4b519
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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