Ethylamine → 2-cyano-N-ethylbenzenesulfonamide

HRID 272786

Reaction equation

HRID 272786 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9](Cl)(=[O:11])=[O:10])#[N:2].[CH2:13]([NH2:15])[CH3:14]>C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH:15][CH2:13][CH3:14])(=[O:11])=[O:10])#[N:2]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 5223472-Cyanobenzenesulfonyl Chloride

Product 1

HCID 73030502-cyano-N-ethylbenzenesulfonamideYield 49.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 2-cyanobenzene-1-sulfonyl chloride (201 mg, 1.00 mmol) in THF (10 mL), a 2M THF solution of ethylamine (5.0 mL, 10.0 mmol) was added. After stirring for 30 min, the reaction was concentrated then purified via preparative HPLC eluting with MeOH/H2O/TFA to provide 2-cyano-N-ethylbenzenesulfonamide (105 mg). The product was dissolved in MeOH (8 mL), conc. HCl (70 mg) was added, and the whole was hydrogenated at 30 psi for 3 h. The reaction was filtered and dried (Na2SO4) to provide 201A (123 mg, 49%). LC-MS: 215.1 (M+H)+.

Workup

  1. concentrationthe reaction was concentrated
  2. customthen purified via preparative HPLC
  3. washeluting with MeOH/H2O/TFA

Sources & evidence

ORD record
ord-687ef267f08440049c0a8627d0f5cd15
Source dataset
uspto-grants-2008_11
Patent number
US07456195B2

Linked notes

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