Ethanol → HCID 86584803, compound

HRID 325048Notes

Reaction equation

HRID 325048 reaction equation
Cl.[NH2:2][OH:3].C([N:6]([CH2:9][CH3:10])CC)C.C(C1C=C[C:16]([CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([N:28]([C:38]([CH3:43])([CH3:42])[P:39](=[O:41])=[O:40])[S:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[O:31])=[O:30])[CH:25]=[CH:26][CH:27]=2)=[CH:15][CH:14]=1)#N.[CH3:44][CH2:45]O>>[NH2:6][C:9]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([N:28]([C:38]([CH3:43])([CH3:42])[P:39](=[O:41])=[O:40])[S:29]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)(=[O:30])=[O:31])[CH:25]=[CH:26][CH:27]=2)=[C:44]([CH:45]=[N:2][OH:3])[CH:10]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 54254962HCID 54254962, compound

Product 1

HCID 86584803HCID 86584803, compoundYield 56%

Procedure

Hydroxylamine hydrochloride (0.018 g; 0.26 mmol) and triethylamine (45 μL, 0.33 mmol) were added to a solution of N-{3-[2-(4-cyanophenyl)-ethoxy]phenyl}-N-(dimethyloxophosphinylmethyl)-benzenesulfonamide (0.090 g; 0.192 mmol; from step (i) above) in EtOH (6 mL). The mixture was heated at reflux for 3 hours, stirred at room temperature overnight and then refluxed for 1 hour. Evaporation of the solvent in vacuo and flash chromatography (SiO2; EtOAc:MeOH (9:1)) afforded 0.054 g (56%) of the sub-title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperaturerefluxed for 1 hour
  4. customEvaporation of the solvent in vacuo and flash chromatography (SiO2; EtOAc:MeOH (9:1))

Sources & evidence

ORD record
ord-0e550d7db112464db1aeccf4dfd78737
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

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