Methane → N-[4-(3-amino-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide

HRID 619061Notes

Reaction equation

HRID 619061 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=3)[N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C>CO.C(OCC)(=O)C.[Pd]>[NH2:23][C:19]1[CH:18]=[C:17]([C:15]2[N:16]=[C:12]([NH:11][S:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)(=[O:10])=[O:9])[S:13][CH:14]=2)[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 2

HCID 297MethaneHCID 42339694-Methyl-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide

Product 1

HCID 21845567N-[4-(3-amino-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamideYield 79.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.5 g of 4-methyl-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide in 150 ml of methanol and 70 ml of ethyl acetate was hydrogenated at room temperature after the addition of 0.15 g of palladium on active charcoal (10%). The catalyst was filtered off and the filtrate was concentrated. Crystallization from ethyl acetate/hexane (1:1) yielded 1.1 g of N-[4-(3-amino-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide as a colorless solid.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated
  4. customCrystallization from ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-7a17ca44e9d84f029026a289298d8fce
Source dataset
uspto-grants-1999_09
Patent number
US05958910

Reaction notes

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