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

HRID 2235494Notes

Reaction equation

HRID 2235494 reaction equation
Br[C:2]1[S:3][C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C(=O)([O-])[O-].[K+].[K+].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>CN(C=O)C.O>[N:20]1([C:2]2[S:3][C:4]3[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 685819982-Bromo-7-nitrobenzo[d]thiazole

Product 1

HCID 685822692-Morpholin-4-yl-7-nitro-1,3-benzothiazoleYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 0.200 g (0.77 mmol) of 2-bromo-7-nitro-1,3-benzothiazole in 2 mL of DMF was added 0.21 g (1.5 mmol) of potassium carbonate and 81 μL (0.93 mmol) of morpholine. The mixture was stirred at room temperature for 72 h and diluted with water. The precipitate that formed was collected by filtration and purified by flash chromatography eluting with a 33% ethyl acetate/hexanes mixture to give 0.075 g (37%) of the title compound as a cream colored powder.

Workup

  1. customThe precipitate that formed
  2. filtrationwas collected by filtration
  3. custompurified by flash chromatography
  4. washeluting with a 33% ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-ec0b41668bcf4aaea98fa7e742a7038d
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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