HCID 12819597, compound → HCID 13260440, compound

HRID 1649519Notes

Reaction equation

HRID 1649519 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-46be68a3e3e0415a9fb42a7b67c17acf
Source dataset
uspto-grants-1983_11
Patent number
US04417917

Reaction notes

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