Phosphorus oxychloride → HCID 118094035, compound

HRID 515544Notes

Reaction equation

HRID 515544 reaction equation
[CH:1]1([NH:6][S:7]([C:10]2[CH:19]=[C:18]([C:20]3[C:21]([CH3:26])=[N:22][O:23][C:24]=3[CH3:25])[CH:17]=[C:16]3[C:11]=2[N:12]=[CH:13][CH:14]=[N+:15]3[O-])(=[O:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:28]=P(Cl)(Cl)Cl>>[CH:1]1([NH:6][S:7]([C:10]2[C:11]3[N:12]=[CH:13][C:14](=[O:28])[NH:15][C:16]=3[CH:17]=[C:18]([C:20]3[C:21]([CH3:26])=[N:22][O:23][C:24]=3[CH3:25])[CH:19]=2)(=[O:8])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 118094030HCID 118094030, compound

Product 1

HCID 118094035HCID 118094035, compound

Procedure

5-(N-cyclopentylsulfamoyl)-7-(3,5-dimethylisoxazol-4-yl)quinoxaline 1-oxide was dissolved in POCl3 and heated to reflux for 1 hour. After cooling to room temperature, volatiles were removed under reduced pressure and dissolved in acetic acid (4 ml). Sodium acetate (100 mg) was added and the solution stirred for 4 hours. Volatiles were removed under reduced pressure and the crude product was purified by preparatory HPLC (5-95% MeCN/H20, 0.1% TFA) to afford the product as a white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. customvolatiles were removed under reduced pressure
  4. dissolutiondissolved in acetic acid (4 ml)
  5. additionSodium acetate (100 mg) was added
  6. customVolatiles were removed under reduced pressure
  7. customthe crude product was purified by preparatory HPLC (5-95% MeCN/H20, 0.1% TFA)

Sources & evidence

ORD record
ord-1ceb4157102e40e0b45b448fb1c83c40
Source dataset
uspto-grants-2015_08
Patent number
US09108953B2

Reaction notes

Loading…