2-Morpholin-4-yl-7-nitro-1,3-benzothiazole → 2-Morpholin-4-yl-1,3-benzothiazol-7-amine

HRID 2235495Notes

Reaction equation

HRID 2235495 reaction equation
[N:1]1([C:7]2[S:8][C:9]3[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>O1CCCC1.[Ni]>[N:1]1([C:7]2[S:8][C:9]3[C:15]([NH2:16])=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 685822692-Morpholin-4-yl-7-nitro-1,3-benzothiazole

Product 1

HCID 685811022-Morpholin-4-yl-1,3-benzothiazol-7-amineYield 33.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 0.075 g (0.28 mmol) of 2-morpholin-4-yl-7-nitro-1,3-benzothiazole in 6 mL of tetrahydrofuran (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 5 h. The catalyst was removed via filtration and the filtrate was concentrated in vacuo. Purification by flash chromatography failed to provide clean B so the 0.022 g (33%) of material thus isolated was used without further purification.

Workup

  1. customThe catalyst was removed via filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customPurification by flash chromatography

Sources & evidence

ORD record
ord-e473b00148bf452999d211fc4779340e
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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