Triethylamine → N,N-dimethyl-N'-(3-cyanomethoxyphenyl)-sulfamide

HRID 618266Notes

Reaction equation

HRID 618266 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[O:5][CH2:6][C:7]#[N:8].C(N(CC)CC)C.[CH3:19][N:20]([CH3:25])[S:21](Cl)(=[O:23])=[O:22]>C1COCC1>[CH3:19][N:20]([CH3:25])[S:21]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:4]([O:5][CH2:6][C:7]#[N:8])[CH:3]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 187896992-(3-Aminophenoxy)acetonitrile

Product 1

HCID 18789586N,N-dimethyl-N'-(3-cyanomethoxyphenyl)-sulfamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-aminophenoxy)-acetonitrile (1.5 g, from Example 1), triethylamine (3.22 mL) in THF (35 mL) was added dimethylsulfamoyl chloride (4.2 mL) dropwise over 10 min. After stirring at room temperature for 1 hr, the solvent was evaporated and the residue was partitioned between dichloromethane and water. The organic layer was washed with 5% HCl solution and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by flash chromatography on silica gel eluting with ethyl acetate:dichloromethane (10:90) to give N,N-dimethyl-N'-(3-cyanomethoxyphenyl)-sulfamide (1.11 g).

Workup

  1. customthe solvent was evaporated
  2. customthe residue was partitioned between dichloromethane and water
  3. washThe organic layer was washed with 5% HCl solution
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by flash chromatography on silica gel eluting with ethyl acetate:dichloromethane (10:90)

Sources & evidence

ORD record
ord-918f02756d204c8faa1621ab4ce8b313
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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