Ammonium Hydroxide → 6-Chloroimidazo[2,1-b][1,3]thiazole-5-sulfonamide

HRID 1484448

Reaction equation

HRID 1484448 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[N:8]([C:9]=1[S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:6][S:5]2.[OH-].[NH4+:15]>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]2[N:8]([C:9]=1[S:10]([NH2:15])(=[O:12])=[O:11])[CH:7]=[CH:6][S:5]2

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 27997176-Chloroimidazo(2,1-b)(1,3)thiazole-5-sulfonyl chloride

Product 1

HCID 27798396-Chloroimidazo[2,1-b][1,3]thiazole-5-sulfonamideYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

2 g (1 mol equiv.) 6-Chloro-imidazo[2,1-b]thiazole-5-sulfonyl chloride was dissolved in 20 mL acetonitrile and cooled to 0° C. Dropwise, 3.7 mL (3 mol equiv.) ammoniumhydroxide was added and the reaction mixture was stirred at room temperature for 10 min, during which a white precipitate was formed. Volatiles were removed under reduced pressure, and the solid residue was washed with water and dried in vacuo affording 1.62 g (88%) 6-chloro-imidazo[2,1-b]thiazole-5-sulfonic acid amide. 1H NMR (400 MHz, DMSO-d6) δ 7.62 (d, J=4.6 1H), 7.98 (d, J=4.6 Hz, 1H), 8.00 (br.s., 2H).

Workup

  1. customwas formed
  2. customVolatiles were removed under reduced pressure
  3. washthe solid residue was washed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d8153386d03442679950960c59e5a202
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Linked notes

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