Water → HCID 57837618, compound

HRID 2264319Notes

Reaction equation

HRID 2264319 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:5]=2[N:6]=1.O1CCCC1.[CH3:19][NH:20][CH3:21].O>O1CCCC1>[CH3:19][N:20]([CH3:21])[C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 114132492-Chloro-5-nitrobenzothiazoleHCID 22320367Dimethylamine tetrahydrofuran

Product 1

HCID 57837618HCID 57837618, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 7.4 ml of tetrahydrofuran was dissolved 160 mg of 2-chloro-5-nitro-1,3-benzothiazole, and thereto was added 1.86 ml of a 1M dimethylamine tetrahydrofuran solution, followed by 16.5 hours of stirring. Water was added to the reaction solution and the organic layer was extracted with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, the solvent was removed by evaporation. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to obtain 173 mg of N,N-dimethyl-5-nitro-1,3-benzothiazol-2-amine as a yellow solid.

Workup

  1. extractionthe organic layer was extracted with ethyl acetate
  2. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed by evaporation
  4. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-ca9526adb8be4aee99eb0aa0db497375
Source dataset
uspto-grants-2010_12
Patent number
US07855198B2

Reaction notes

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