Ammonia → 2-Methyl-3-nitrobenzenesulfonamide

HRID 1995401Notes

Reaction equation

HRID 1995401 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH3:11].N([O-])=O.[Na+].S(=O)=O.N.COC1C(C)=C([S:28]([NH2:31])(=[O:30])=[O:29])C=CC=1>S(=O)(=O)(O)O.O.C(O)(=O)C.[Cu](Cl)Cl>[CH3:11][C:3]1[C:4]([N+:8]([O-:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=1[S:28]([NH2:31])(=[O:30])=[O:29]

Participants

10

Reactant 5

HCID 222AmmoniaHCID 1119Sulfur DioxideHCID 117832-Methyl-3-nitroanilineHCID 155671703-Methoxy-2-methylbenzenesulfonamideHCID 23668193Sodium Nitrite

Product 1

HCID 235400232-Methyl-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 4

HCID 24014Cupric ChlorideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent3×HCID 1118Sulfuric AcidSolvent

Procedure

7.5 gm (49 mmols) of 2-amino-6-nitro-toluene were dissolved in a mixture of 27.5 gm of concentrated sulfuric acid and 250 ml of water, and the solution was diazotized with a solution of 3.75 gm (54 mmols) of sodium nitrite in 7.5 ml of water at 0° to 5° C. After 2 hours the reaction mixture was added in portions to a previously prepared mixture of 90 ml of a sulfur dioxide solution in glacial acetic acid and a solution of 1.5 gm of copper(II)chloride in 4 ml of water at 20° C. The further treatment and the reaction with ammonia was carried out analogous to the method described for the preparation of 3-methoxy-2-methylbenzene sulfonamide (Example 8).

Workup

  1. customat 20° C

Sources & evidence

ORD record
ord-91d7f642ebaa495c9c6022638a5e0969
Source dataset
uspto-grants-1983_09
Patent number
US04404230

Reaction notes

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