1-Chloro-2,4-Dinitrobenzene → 5-Nitro-1,3-benzothiazol-2-amine

HRID 1383055Notes

Reaction equation

HRID 1383055 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1Cl)([O-])=O.[NH2:14][C:15](N)=[S:16].O>N1C=CC=CC=1>[NH2:14][C:15]1[S:16][C:5]2[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=2[N:1]=1

Participants

5

Reactant 3

HCID 61-Chloro-2,4-DinitrobenzeneHCID 962WaterHCID 2723790Thiourea

Product 1

HCID 27547595-Nitro-1,3-benzothiazol-2-amineYield 118.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 10.13 g of 2,4-dinitrochlorobenzene and 15.2 g of thiourea in 50 ml of pyridine is boiled, with stirring, under a reflux condenser for 3 hours. After cooling, the mixture is thoroughly stirred with 500 ml of water, and the solid is filtered off with suction, washed with water and dried. 11.6 g of 2-amino-5-nitrobenzothiazole having a purity of 66% by HPLC analysis, corresponding to a yield of 78.5% of theory, are obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid is filtered off with suction
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-6bef2e9519c14c8da67cf316669a861e
Source dataset
uspto-grants-1989_02
Patent number
US04808723

Reaction notes

Loading…