Ammonia → 5-(Tert-butyl)-2-methoxybenzenesulfonamide

HRID 543384Notes

Reaction equation

HRID 543384 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:13](Cl)(=[O:15])=[O:14])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)([CH3:4])[CH3:3].[NH3:17]>CC(C)=O>[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:13]([NH2:17])(=[O:15])=[O:14])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 132102315-tert-Butyl-2-methoxybenzene-1-sulfonyl chloride

Product 1

HCID 109336945-(Tert-butyl)-2-methoxybenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

25.3 g (0.1 mol) of 3-(1,1-dimethylethyl)-6-methoxybenzenesulfonyl chloride are dissolved in a little acetone and slowly added dropwise to 100 ml of concentrated ammonia solution at room temperature. The mixture is stirred at room temperature for 30 minutes and then poured onto ice-water. After acidification with concentrated hydrochloric acid, the product is filtered off with suction. Isopropanol is used for recrystallization. White crystals of melting point 156°-158° C.

Workup

  1. additionpoured onto ice-water
  2. filtrationAfter acidification with concentrated hydrochloric acid, the product is filtered off with suction
  3. customIsopropanol is used for recrystallization

Sources & evidence

ORD record
ord-19009a8660254981a33a23cf4fadc1e1
Source dataset
uspto-grants-1987_04
Patent number
US04661636

Reaction notes

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