Water → 4-Sulfamoylanilino-alpha-[4-(2-furyl)phenyl]acetnitrile

HRID 497193Notes

Reaction equation

HRID 497193 reaction equation
[S:1]([C:5]1[CH:23]=[CH:22][C:8]([N:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])(=[O:3])[NH2:2].C[Si]([C:28]#[N:29])(C)C.O>C1COCC1.[Cl-].[Zn+2].[Cl-]>[S:1]([C:5]1[CH:23]=[CH:22][C:8]([NH:9][CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)=[CH:13][CH:12]=2)[C:28]#[N:29])=[CH:7][CH:6]=1)(=[O:4])(=[O:3])[NH2:2]

Participants

6

Reactant 3

HCID 962WaterHCID 82115Trimethylsilyl cyanideHCID 223167314-sulfamoyl-N-[4-(2-furyl)benzylidene]aniline

Product 1

HCID 223169454-Sulfamoylanilino-alpha-[4-(2-furyl)phenyl]acetnitrileYield 72.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-sulfamoyl-N-[4-(2-furyl)benzylidene]aniline (0.37 g, 1.13 mmol) in anhydrous THF (5 mL) at 0° C. was added trimethylsilyl cyanide (0.135 g, 1.36 mmol), zinc chloride (1.36 mL, 1.0 M solution in ether, 1.36 mmol). The temperature of the reaction mixture was then allowed to return to room temperature, and the mixture was stirred overnight. The reaction mixture was poured into water and the whole was extracted with ethyl acetate (20 mL×2). The organic layer was washed with brine, dried over Na2SO4, and concentrated to give the subtitle compound (0.288 g). 1H-NMR (DMSO-d6) δ: 7.84-7.78 (m, 3H), 7.65-7.60 (m, 4H), 7.39 (d, J=9 Hz, 1H), 7.04-7.01 (m, 3H), 6.91 (d, J=9 Hz, 2H), 6.62 (dd, J=3, 2 Hz, 1H), 6.16 (d, J=9 Hz, 1H). MS (EI) m/z 353 (M+)

Workup

  1. customto return to room temperature
  2. extractionthe whole was extracted with ethyl acetate (20 mL×2)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f7d4c031f1424a55a88ef0a126c8605f
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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