2-nitrobenzyl-N,N-dimethylsulfonamide → HCID 13178727, compound

HRID 434459Notes

Reaction equation

HRID 434459 reaction equation
[CH3:1][N:2]([CH3:16])[S:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O)(=[O:5])=[O:4]>[Pd].COCCOCCOC>[CH3:1][N:2]([CH3:16])[S:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13])(=[O:4])=[O:5]

Participants

4

Reactant 1

HCID 131787262-nitrobenzyl-N,N-dimethylsulfonamide

Product 1

HCID 13178727HCID 13178727, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8150DiglymeSolvent

Procedure

In a pressure bottle, a mixture of 116 g of the product of Example 2, 1400 ml of 2-methoxyethyl ether and 10 g of 10% palladium on carbon was shaken at 110° under 500 p.s.i. hydrogen until the hydrogen was no longer absorbed. The catalyst was filtered off and the filtrate stripped under reduced pressure to a volume of 200 ml. This residue was poured into 600 ml of ice and the precipitate filtered off and dried to give 84 g of crude product, m.p. 70°-78°. Recrystallization from ~600 ml of 1-chlorobutane gave 60.6 g of N,N-dimethyl-2-aminobenzenemethanesulfonamide, m.p. 92°-100°.

Workup

  1. customhydrogen until the hydrogen was no longer absorbed
  2. filtrationThe catalyst was filtered off
  3. additionThis residue was poured into 600 ml of ice
  4. filtrationthe precipitate filtered off
  5. customdried
  6. customto give 84 g of crude product, m.p. 70°-78°
  7. customRecrystallization from ~600 ml of 1-chlorobutane

Sources & evidence

ORD record
ord-89757d506d034fa79c368b7ebfdad4ee
Source dataset
uspto-grants-1983_08
Patent number
US04397679

Reaction notes

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