Hydrochloric Acid → 5-Benzothiazolesulfonic acid, 2-amino-

HRID 2219995Notes

Reaction equation

HRID 2219995 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-])=O.S(=O)(=O)(O)O.[NH4+].[N:21]#[C:22][S-:23].Cl>[Fe].O>[NH2:21][C:22]1[S:23][C:2]2[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][C:3]=2[N:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 15666Ammonium thiocyanateHCID 69227Benzenesulfonic acid, 4-amino-3-nitro-

Product 1

HCID 120978195-Benzothiazolesulfonic acid, 2-amino-

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Procedure

218 g 2-amino-nitrobenzene-5-sulfonic acid were added to 1100 ml of a 1.0 Molar Sulphuric acid at 5° C. and diazotated. The resulting suspension was slowly added to a solution of 180 ml water, 152 g NH4SCN and 5 g Cu(SCN)2 at 0 to 5° C. and stirred for additional 3 hours at room temperature. The reaction mixture was poured into a hot (90 to 95° C.) suspension of 1000 ml water, 500 g iron powder and 17 g of a 37% hydrochloric acid and the resulting suspension was stirred till the reduction was completed. The mixtures was brought to a pH of more than 9 and the iron slurry was filtered off. The product was precipitated by lowering the pH, filtered off, washed and dryed. This yields 200 g product (2-Amino-benzthiazole-5-sulfonic acid) as an press cake.

Workup

  1. stirringthe resulting suspension was stirred till the reduction
  2. filtrationthe iron slurry was filtered off
  3. customThe product was precipitated
  4. filtrationfiltered off
  5. washwashed

Sources & evidence

ORD record
ord-ad2d2919b02f45c38168057bd3fae31d
Source dataset
uspto-grants-2008_08
Patent number
US07416593B2

Reaction notes

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