2,4,6-Trimethyl-N-(7-nitro-1,3-benzothiazol-2-yl)benzamide → N-(7-Amino-1,3-benzothiazol-2-yl)-2,4,6-trimethylbenzamide

HRID 2235500Notes

Reaction equation

HRID 2235500 reaction equation
[CH3:1][C:2]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:5]>C1COCC1.[Ni]>[NH2:16][C:15]1[C:9]2[S:8][C:7]([NH:6][C:4](=[O:5])[C:3]3[C:19]([CH3:24])=[CH:20][C:21]([CH3:23])=[CH:22][C:2]=3[CH3:1])=[N:11][C:10]=2[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 860492022,4,6-Trimethyl-N-(7-nitro-1,3-benzothiazol-2-yl)benzamide

Product 1

HCID 86049206N-(7-Amino-1,3-benzothiazol-2-yl)-2,4,6-trimethylbenzamideYield 65%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 0.200 (0.586 mmol) of 2,4,6-trimethyl-N-(7-nitro-1,3-benzothiazol-2-yl)benzamide in 5 mL of THF was added a pipet tip of Raney nickel. The reaction was kept under a hydrogen atmosphere via a balloon and stirred at room temperature for 90 min. The catalyst was removed via filtration and the filtrate was concentrated in vacuo to give a burnt orange solid. The resulting crude solid was purified by flash chromatography eluting with 25% ethyl acetate/hexanes mixture to give 0.118 g (65%) of the title compound as a light yellow powder.

Workup

  1. customThe catalyst was removed via filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto give a burnt orange solid
  4. customThe resulting crude solid was purified by flash chromatography
  5. washeluting with 25% ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-f685a1acb77e4e67b0ddde6212b893c1
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

Loading…