Ammonia → Ammonia

HRID 731216

Reaction equation

HRID 731216 reaction equation
[Na].[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[S:12]([OH:15])(=O)=[O:13].S(Cl)(Cl)(=O)=O.P(Cl)(Cl)(Cl)=O.S1(CCCC1)(=O)=O.[NH3:33]>CO>[NH3:2].[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[S:12]([NH2:33])(=[O:15])=[O:13]

Participants

9

Reactant 6

HCID 222AmmoniaHCID 24648Sulfuryl chlorideHCID 24813Phosphorus oxychlorideHCID 31347SulfolaneHCID 66786Benzenesulfonic acid, 2-amino-5-nitro-HCID 5360545Sodium

Product 2

HCID 222AmmoniaHCID 153583862-Amino-5-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The commercially available sodium salt of 2-amino-5-nitro-benzenesulfonic acid can be converted to the corresponding sulfonyl chloride with phosphoryl chloride in the presence of a suitable co-solvent, such as sulfolane. Treatment with ammonia, e.g., ammonia solution in methanol or ammonia gas, affords the desired 2-amino-5-nitro-benzenesulfonamide intermediate.

Sources & evidence

ORD record
ord-f167e916d5f747d49eea0772ec8a6052
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Linked notes

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