Thionyl Chloride → 5-Chloro-6-nitro-2,1,3-benzothiadiazole

HRID 533582Notes

Reaction equation

HRID 533582 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:12])[C:5]([NH2:11])=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[S:13](Cl)(Cl)=O.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]2=[N:11][S:13][N:12]=[C:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 57026184-Chloro-5-nitro-o-phenylenediamine

Product 1

HCID 895860075-Chloro-6-nitro-2,1,3-benzothiadiazoleYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution obtained by dissolving 4-chloro-5-nitrobenzene-1,2-diamine (1) (15 g, 0.0799 mol) in 500 mL of dichloromethane (DCM) is cooled down to 0° C., and thionyl chloride (SOCl2, 11.7 mL, 0.159 mol, 2.0 eq) is slowly dripped into the solution. The reactant is agitated and reflowed for 16 hours, cooled down to room temperature, and condensed under a reduced pressure. The condensate is dissolved again in dichloromethane, cleaned with a saturated NaHCO3 aqueous solution, and subfractionated. An organic layer is dried, condensed under a reduced pressure, and passed through a silica column so as to obtain thin brown solid-phase compound (2) (15 g, yield: 87%). 1H NMR (400 MHz, CDCl3): δ ppm 8.49 (s, 1H), 8.26 (s, 1H).

Workup

  1. customA solution obtained
  2. temperaturecooled down to room temperature
  3. customcondensed under a reduced pressure
  4. customAn organic layer is dried
  5. customcondensed under a reduced pressure

Sources & evidence

ORD record
ord-c002fc91453247a29701732499074594
Source dataset
uspto-grants-2014_10
Patent number
US08853347B2

Reaction notes

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