Methane → 4-Sulfobenzenediazonium hydroxide

HRID 1898753Notes

Reaction equation

HRID 1898753 reaction equation
[S:1]([OH:11])(=[O:10])([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)=[O:2].C.C1C(Br)=C(Br)[NH:15]C=1C(O)=O.N([O-])=O.[Na+]>O>[OH-:2].[S:1]([C:3]1[CH:4]=[CH:5][C:6]([N+:9]#[N:15])=[CH:7][CH:8]=1)([OH:11])(=[O:10])=[O:2]

Participants

6

Reactant 4

HCID 297MethaneHCID 8479Sulfanilic acidHCID 1618304,5-Dibromo-2-Pyrrolic AcidHCID 23668193Sodium Nitrite

Product 1

HCID 227152964-Sulfobenzenediazonium hydroxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sulfanilic acid (43 g) was dissolved in 2 L of water with warming. The solution was mixed with 200 g of a carbon black having a surface area of 230 m2 /g and a DBPA of 70 ml/100 g and allowed to cool. An aqueous solution of 20.5 g NaNO2 was added slowly and the resulting dispersion was stirred for one hour. 4-Sulfobenzenediazonium hydroxide inner salt was formed in situ, which reacted with the carbon black. The dispersion was filtered through a Whatman #41 filter, and the product was dried in an oven at 70° C. The product has attached p--C6H4SO3- groups.

Workup

  1. temperaturewith warming
  2. temperatureto cool

Sources & evidence

ORD record
ord-a7bb598f3656488aaec456d3cdfecd9e
Source dataset
uspto-grants-1996_11
Patent number
US05571311

Reaction notes

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