Phosphorus oxychloride → 2-{2-{[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}pentanenitrile

HRID 1604698Notes

Reaction equation

HRID 1604698 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([C:10]1[N:11]=[C:12]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4[CH:39]=[CH:38][CH:37]=[CH:36][C:27]=4[O:28][CH:29]([CH2:33][CH2:34][CH3:35])[C:30]([NH2:32])=O)=[CH:20][C:18]=3[CH:19]=2)[S:13][CH:14]=1)([CH3:9])([CH3:8])[CH3:7]>CN(C)C=O>[C:6]([C:10]1[N:11]=[C:12]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4[CH:39]=[CH:38][CH:37]=[CH:36][C:27]=4[O:28][CH:29]([CH2:33][CH2:34][CH3:35])[C:30]#[N:32])=[CH:20][C:18]=3[CH:19]=2)[S:13][CH:14]=1)([CH3:7])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 196038242-{2-{[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}-pentanamide

Product 1

HCID 196037652-{2-{[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}pentanenitrileYield 92.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorus oxychloride (245 mg) was dissolved in dimethylformamide (2 ml) and the solution was ice-cooled. To this solution was added 2-{2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy]pentanamide (510 mg), and the mixture was stirred for two hours at room temperature. The reaction mixture was concentrated, diluted with water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give 2-{2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}pentanenitrile (453 mg).

Workup

  1. temperaturecooled
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9b3c7045d30546588efb10f115bb8275
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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