Hydrochloric Acid → 2-Chloro-p-toluidine-5-sulfonic acid

HRID 2292988Notes

Reaction equation

HRID 2292988 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[S:11]([OH:14])(=[O:13])=[O:12].COC1C(N)=CC=CC=1.[ClH:24].N([O-])=O.[I-].[K+]>O>[NH2:3][C:4]1[CH:9]=[C:8]([Cl:24])[C:7]([CH3:10])=[CH:6][C:5]=1[S:11]([OH:14])(=[O:12])=[O:13]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 946NitriteHCID 4875Potassium IodideHCID 69342-Amino-5-methylbenzenesulfonic acidHCID 70002-MethoxyanilineHCID 14798Sodium Hydroxide

Product 1

HCID 69352-Chloro-p-toluidine-5-sulfonic acidYield 84.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 11.2 grams of 50% sodium hydroxide solution, 13.4 grams of 2-amino-5-methyl-benzene sulfonic acid .[.(o-anisidine).]. and 13.4 grams of 2-amino-4-chloro-5-methyl benzene sulfonic acid is prepared, and 300 ml. of water is added with stirring until clear. Ice is added to a volume of 488 ml. and the temperature is 0°±2° C., Concentrated hydrochloric acid (36.2 grams) is added with stirring over a period of 4 to 6 minutes. A solution of 10 grams of sodium nitride and 20 ml. of water is added, and the resulting mixture is stirred for 15 minutes at 10°-12° C. while testing for excess acid with Congo Red and for nitrite with potassium iodide paper.

Workup

  1. additionIce is added to a volume of 488 ml
  2. customis 0°±2° C.
  3. stirringwith stirring over a period of 4 to 6 minutes
  4. stirringthe resulting mixture is stirred for 15 minutes at 10°-12° C.

Sources & evidence

ORD record
ord-aba196da9d2c4b19b68532f2bd5ccd82
Source dataset
uspto-grants-1997_11
Patent number
USRE035654

Reaction notes

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