Methylamine → N-Methyl-6-nitrobenzo[D]thiazol-2-amine

HRID 1174960

Reaction equation

HRID 1174960 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:14][NH2:15]>C1COCC1.O>[CH3:14][NH:15][C:2]1[S:3][C:4]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 754762-Chloro-6-nitrobenzothiazole

Product 1

HCID 638568N-Methyl-6-nitrobenzo[D]thiazol-2-amineYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Place 2-chloro-6-nitro-benzothiazole (5.82 g, 27.1 mmol) in THF (130 mL). Add 40% methylamine in water (7 mL) and stir until the product precipitates out. Concentrate in vacuo and then triturate with methanol. Filter off the product and wash with methanol, Dry thoroughly to yield 4.99 g (88%) of the title compound: mass spectrum (ion-spray): (m/z)=210.0 (M+1).

Workup

  1. customprecipitates out
  2. concentrationConcentrate in vacuo
  3. customtriturate with methanol
  4. filtrationFilter off the product
  5. washwash with methanol
  6. customDry thoroughly

Sources & evidence

ORD record
ord-d63f6ac0ae0d46888a58e608370ee763
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Linked notes

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