Benzo(d)thiazol-2-amine → N-Benzothiazol-2-yl-2-methoxy-acetamide

HRID 1087458Notes

Reaction equation

HRID 1087458 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:11][O:12][CH2:13][C:14](Cl)=[O:15]>N1C=CC=CC=1>[CH3:11][O:12][CH2:13][C:14]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1)=[O:15]

Participants

4

Reactant 2

HCID 8706Benzo(d)thiazol-2-amineHCID 96623Methoxyacetyl chloride

Product 1

HCID 667540N-Benzothiazol-2-yl-2-methoxy-acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Aminobenzothiazole (4.5 g) is dissolved in pyridine (100 ml) and thereto is added dropwise methoxyacetyl chloride (3.0 ml) at room temperature. After the mixture is stirred at room temperature for 2 hours, the solvent is distilled off. The resulting oil is dissolved in chloroform and the organic layer is washed with water and then with a saturated saline. The organic layer is dried over anhydrous sodium sulfate and the solvent is distilled off. The resulting solids are recrystallized from ethanol/water to give the title compound (5.2 g) having the following physical properties.

Workup

  1. distillationthe solvent is distilled off
  2. dissolutionThe resulting oil is dissolved in chloroform
  3. washthe organic layer is washed with water
  4. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  5. distillationthe solvent is distilled off
  6. customThe resulting solids are recrystallized from ethanol/water

Sources & evidence

ORD record
ord-3e43672404ed4e4bbeb2b2ceb84a8e92
Source dataset
uspto-grants-1991_07
Patent number
US05036086

Reaction notes

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