Benzene-1,2-disulfonyl diazide → Benzene-1,2-disulfonamide

HRID 1906344Notes

Reaction equation

HRID 1906344 reaction equation
[C:1]1([S:13]([N:16]=[N+]=[N-])(=[O:15])=[O:14])[C:2]([S:7]([N:10]=[N+]=[N-])(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[BH4-].[Na+]>C(O)C>[C:1]1([S:13]([NH2:16])(=[O:15])=[O:14])[C:2]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 3555379Benzene-1,2-disulfonyl diazideHCID 4311764Sodium borohydride

Product 1

HCID 13885364Benzene-1,2-disulfonamideYield 97.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

One gram of 1,2-benzenedisulfonylazide was added portionwise to 0.4 gm sodium borohydride in 15 ml of ethyl alcohol with stirring and cooling. After addition, the mixture was stirred with cooling (ice/acetone bath) for 2 hours and filtered. The solid was washed with cold ethyl alcohol and ether to yield 0.8 g of 1,2-benzenedisulfonamide, m.p. 250° C. Mass spec. (M/e) 236.

Workup

  1. temperaturecooling
  2. additionAfter addition
  3. stirringthe mixture was stirred
  4. filtrationfiltered
  5. washThe solid was washed with cold ethyl alcohol and ether

Sources & evidence

ORD record
ord-2a6b93f22f6447809682333cf507f18c
Source dataset
uspto-grants-1987_03
Patent number
US04652304

Reaction notes

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