Hydroxyamine hydrochloride → 2-{2-{[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}pentanamide oxime

HRID 1604700Notes

Reaction equation

HRID 1604700 reaction equation
Cl.[OH:2][NH2:3].C[O-].[Na+].[C:7]([C:11]1[N:12]=[C:13]([C:16]2[O:17][C:18]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]4[CH:39]=[CH:38][CH:37]=[CH:36][C:28]=4[O:29][CH:30]([CH2:33][CH2:34][CH3:35])[C:31]#[N:32])=[CH:21][C:19]=3[CH:20]=2)[S:14][CH:15]=1)([CH3:10])([CH3:9])[CH3:8]>CS(C)=O.CO>[C:7]([C:11]1[N:12]=[C:13]([C:16]2[O:17][C:18]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]4[CH:39]=[CH:38][CH:37]=[CH:36][C:28]=4[O:29][CH:30]([CH2:33][CH2:34][CH3:35])[C:31](=[N:3][OH:2])[NH2:32])=[CH:21][C:19]=3[CH:20]=2)[S:14][CH:15]=1)([CH3:8])([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 196037652-{2-{[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}pentanenitrile

Product 1

HCID 867548822-{2-{[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}pentanamide oximeYield 110.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

Hydroxyamine hydrochloride (174 mg) was dissolved in dimethylsulfoxide (2 ml) and 28% solution of sodium methoxide in methanol (0.125 g) was added into it. The mixture was stirred for ten minutes at room temperature. 2-{2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}-pentanenitrile (224 mg) was added into the solution and the resulting mixture was stirred at 80° C. for an hour. The reaction mixture was collected and diluted with water and was extracted with ethyl acetate. The organic layer was washed with brine and was dried over magnesium sulfate. Concentration gave 2-{2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}pentanamide oxime as an amorphous solid (266 mg).

Workup

  1. stirringthe resulting mixture was stirred at 80° C. for an hour
  2. customThe reaction mixture was collected
  3. additiondiluted with water
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialwas dried over magnesium sulfate
  7. concentrationConcentration

Sources & evidence

ORD record
ord-63372f480b2b49fdb3c2e0d8737f4b29
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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