Triethylamine → 3-bromo-N-butyl-5-formyl-4-methoxy-benzenesulfonamide

HRID 1752875Notes

Reaction equation

HRID 1752875 reaction equation
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH:11]=[O:12])[CH:5]=[C:6]([CH:10]=1)C(Cl)=O.[CH2:15]([NH:19][SH:20](=[O:22])=[O:21])[CH2:16][CH2:17][CH3:18].C(N(CC)CC)C>ClCCl>[Br:1][C:2]1[CH:10]=[C:6]([S:20]([NH:19][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:22])=[O:21])[CH:5]=[C:4]([CH:11]=[O:12])[C:3]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 866076925-Bromo-3-formyl-4-methoxybenzoyl chlorideHCID 178449956HCID 178449956, compound

Product 1

HCID 866077083-bromo-N-butyl-5-formyl-4-methoxy-benzenesulfonamideYield 103.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Bromo-3-formyl-4-methoxybenzoyl chloride (501 mg, 1.8 mmol) was dissolved in in dichloromethane (5 mL) and the solution was added dropwise to a vigorously stirring solution of N-butylsulfonamide (272 mg, 2.0 mmol), triethylamine (2.5 mmol) and a catalytic amount of N,N′-dimethylaminopyridine (10 mL in dichloromethane). The mixture was stirred at room temperature until the reaction was complete and concentrated under reduced pressure. The residue was partitioned between 5% citric acid and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and the filtrate was evaporated to give 3-bromo-N-butyl-5-formyl-4-methoxy-benzenesulfonamide as a white solid (650 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between 5% citric acid and ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-633470c241764e8d963d49c43953b78b
Source dataset
uspto-grants-2015_10
Patent number
US09162986B2

Reaction notes

Loading…