Water → 5-Nitro-1,3-benzothiazol-2-amine

HRID 1383057Notes

Reaction equation

HRID 1383057 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[S:13][C:14]#[N:15])([O-])=O.NC(N)=S.O>CN(C)C=O>[NH2:15][C:14]1[S:13][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 962WaterHCID 153252,4-Dinitrophenyl thiocyanateHCID 2723790Thiourea

Product 1

HCID 27547595-Nitro-1,3-benzothiazol-2-amineYield 108.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

11.71 g of 2,4-dinitrophenyl thiocyanate are added, over the course of 15 minutes, to a solution of 7.6 g of thiourea in 50 ml of dimethylformamide at 150° C. The mixture is stirred at 150° C. for a further 2 hours, and the product is discharged into 500 ml of water, and the solid is filtered off with suction and washed with water. 11 g of crude 2-amino-5-nitrobenzothiazole are obtained, its identity being confirmed by TLC comparison with authentic material.

Workup

  1. filtrationthe solid is filtered off with suction
  2. washwashed with water

Sources & evidence

ORD record
ord-e618ef3387024ac6b922bc412026e6e8
Source dataset
uspto-grants-1989_02
Patent number
US04808723

Reaction notes

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