4,7-Dibromo-2,1,3-benzothiadiazole → 3,6-Dibromobenzene-1,2-diamine

HRID 1765961Notes

Reaction equation

HRID 1765961 reaction equation
[Br:1][C:2]1[C:10]2[C:6](=[N:7]S[N:9]=2)[C:5]([Br:11])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[NH2:9][C:10]1[C:2]([Br:1])=[CH:3][CH:4]=[C:5]([Br:11])[C:6]=1[NH2:7]

Participants

4

Reactant 2

HCID 6263614,7-Dibromo-2,1,3-benzothiadiazoleHCID 4311764Sodium borohydride

Product 1

HCID 118215323,6-Dibromobenzene-1,2-diamineYield 79.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4,7-dibromo-2,1,3-benzothiadiazole (synthesized according to as described in K. Pilgram, J. Heterocycl. Chem., 7 (1970), 629) (16.0 g, 54.4 mmol) and NaBH4 (38.1 g, 1.0 mol) in 500 ml ethanol was stirred at room temperature for 30 hours. The solvent was evaporated and the residue mixed with 500 ml water. The obtained mixture was extracted into diethyl ether (5×150 ml). The combined extracts were washed with brine (2×100 ml) and dried over anhydrous Na2SO4. Evaporation of the solvent and drying under reduced pressure afforded 11.5 g (79.5%) of the product.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue mixed with 500 ml water
  3. extractionThe obtained mixture was extracted into diethyl ether (5×150 ml)
  4. washThe combined extracts were washed with brine (2×100 ml)
  5. dry with materialdried over anhydrous Na2SO4
  6. customEvaporation of the solvent
  7. customdrying under reduced pressure

Sources & evidence

ORD record
ord-374a22ccac464e958292f5a572e96171
Source dataset
uspto-grants-2007_06
Patent number
US07229943B2

Reaction notes

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