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

HRID 396761
Notes
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Reaction equation

HRID 396761 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 3007855ZincchlorideCatalyst
HCID 8028
Tetrahydrofuran
Solvent

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).

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-5e2100a86390408d9923e62bc38dceac
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06608095B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes