Tert-Butylamine → 5-t-butyl-2-methoxy-3-nitrophenyl N-t-butyl sulfonamide

HRID 1651475Notes

Reaction equation

HRID 1651475 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[C:6]([C:10]1[CH:11]=[C:12]([N+:22]([O-:24])=[O:23])[C:13]([O:20][CH3:21])=[C:14]([S:16](Cl)(=[O:18])=[O:17])[CH:15]=1)([CH3:9])([CH3:8])[CH3:7]>C(#N)C>[C:6]([C:10]1[CH:11]=[C:12]([N+:22]([O-:24])=[O:23])[C:13]([O:20][CH3:21])=[C:14]([S:16]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:17])=[O:18])[CH:15]=1)([CH3:9])([CH3:7])[CH3:8]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 15029584HCID 15029584, compound

Product 1

HCID 150295855-t-butyl-2-methoxy-3-nitrophenyl N-t-butyl sulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

t-Butylamine (9 ml) was added to a cooled solution of 5-t-butyl-2-methoxy-3-nitrophenyl sulfonyl chloride (7.4 g) in acetonitrile (40 ml). The mixture was stirred at ambient temperature for 1 hour and then the solvent was removed under vacuum. The residue was shaken with ethyl acetate (100 ml) and 4% citric acid (100 ml). The organic phase was separated and dried over sodium sulphate. Evaporation of solvent gave a solid residue which was recrystallized from aqueous ethanol to give the title compound (6.0 g);

Workup

  1. customthe solvent was removed under vacuum
  2. stirringThe residue was shaken with ethyl acetate (100 ml) and 4% citric acid (100 ml)
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulphate
  5. customEvaporation of solvent
  6. customgave a solid residue which
  7. customwas recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-9628ff5013cb4231a66d02b35c6cd874
Source dataset
uspto-grants-1990_05
Patent number
US04929269

Reaction notes

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