3-Fluoro-p-anisaldehyde → N-tert-Butyl-4-((3-fluoro-4-methoxybenzylidene)amino)benzenesulfonamide

HRID 446156Notes

Reaction equation

HRID 446156 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH:20]=O>C1(C)C=CC=CC=1>[C:12]([NH:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([N:1]=[CH:20][C:19]2[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:17]([F:16])[CH:18]=2)=[CH:3][CH:4]=1)(=[O:10])=[O:9])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 676963-Fluoro-p-anisaldehydeHCID 8326274-Amino-N-(1,1-dimethylethyl)benzenesulfonamide

Product 1

HCID 11132250N-tert-Butyl-4-((3-fluoro-4-methoxybenzylidene)amino)benzenesulfonamideYield 99.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-amino-N-tert-butylbenzenesulfonamide (52.3 g, 0.23 mol, obtained in example 1), 3-fluoro-4-methoxybenzaldehyde (35.3 g, 0.23 mol) and toluene (2.5 L) is heated at reflux in a Dean-Stark for 24 h. The solvent is removed, yielding 83.5 g of the title compound (yield: quantitative).

Workup

  1. temperatureis heated
  2. temperatureat reflux in a Dean-Stark for 24 h
  3. customThe solvent is removed

Sources & evidence

ORD record
ord-0f6eeaf6bd2042379f3472ee7a9ddbb7
Source dataset
uspto-grants-2013_07
Patent number
US08476456B2

Reaction notes

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