Hydrochloric Acid → 5-Amino-6-chloro-2,1,3-benzothiadiazole

HRID 533583Notes

Reaction equation

HRID 533583 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][C:5]2=[N:6][S:7][N:8]=[C:4]2[CH:3]=1.O.O.Cl[Sn]Cl.Cl.C([O-])(O)=O.[Na+]>CO.ClCCl.O>[Cl:1][C:2]1[C:10]([NH2:11])=[CH:9][C:5]2[C:4]([CH:3]=1)=[N:8][S:7][N:6]=2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 895860075-Chloro-6-nitro-2,1,3-benzothiadiazole

Product 1

HCID 895860045-Amino-6-chloro-2,1,3-benzothiadiazoleYield 95.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution is prepared by dissolving a compound (2) (16.8 g, 0.0779 mol) in methanol (800 mL), and SnCl2.2H2O (87 g, 0.389 mol, 5.0 eq), water (80 mL) and 1N HCl (30 mL) are sequentially put into the solution. The reactant is agitated and reflowed overnight, cooled down to room temperature (24° C.), and condensed under a reduced pressure. The condensate is dissolved in dichloromethane, neutralized with a saturated NaHCO3 aqueous solution, and then passed through Celite. An organic layer is dried and condensed under a reduced pressure so as to obtain a yellow solid-phase compound (3) (13.8 g, yield: 95%). 1H NMR (400 MHz, CDCl3): δ ppm 7.99 (s, 1H), 7.14 (s, 1H), 4.54 (br s, 2H).

Workup

  1. customA solution is prepared
  2. custom(24° C.), and condensed under a reduced pressure
  3. customAn organic layer is dried
  4. customcondensed under a reduced pressure so as

Sources & evidence

ORD record
ord-161ae6430c9e4d83bc62033808c71f67
Source dataset
uspto-grants-2014_10
Patent number
US08853347B2

Reaction notes

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