HCID 12819597, compound → HCID 13260440, compound

HRID 1105753Notes

Reaction equation

HRID 1105753 reaction equation
[CH3:1][N:2]([CH3:19])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=1[N+:16]([O-])=O)(=[O:5])=[O:4].[H][H]>[Pd].C(OCC)(=O)C>[NH2:16][C:7]1[CH:8]=[C:9]([C:12]([F:14])([F:13])[F:15])[CH:10]=[CH:11][C:6]=1[S:3]([N:2]([CH3:19])[CH3:1])(=[O:4])=[O:5]

Participants

5

Reactant 2

HCID 12819597HCID 12819597, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 13260440HCID 13260440, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a pressure vessel, 109 g of N,N-dimethyl-2-nitro-4-(trifluoromethyl)benzenesulfonamide, 250 ml of ethyl acetate and 5 g of 10% palladium-on-carbon were shaken at 130° under 500 psi hydrogen pressure until no more hydrogen was absorbed, as determined by no additional pressure drop. The reaction mixture was cooled and the catalyst filtered off. The solution was stripped in vacuo to give 95.2 g of 2-amino-N,N-dimethyl-4-(trifluoromethyl)benzenesulfonamide as a slowly crystalizing oil, m.p. 65°-70° C.

Workup

  1. customwas absorbed
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe catalyst filtered off

Sources & evidence

ORD record
ord-c642f010e01440f184334ec5c59db763
Source dataset
uspto-grants-1982_01
Patent number
US04310346

Reaction notes

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