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

HRID 1383056Notes

Reaction equation

HRID 1383056 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.[S-:14][C:15]#[N:16].[NH4+].O>S1(CCCC1)(=O)=O>[NH2:16][C:15]1[S:14][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 15666Ammonium thiocyanate

Product 1

HCID 27547595-Nitro-1,3-benzothiazol-2-amineYield 134.7%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 5.06 g of 2,4-dinitrochlorobenzene and 7.6 g of ammonium thiocyanate in 25 ml of sulpholane is heated, with stirring, to 150° C. and maintained at this temperature for 1.5 hours. The product is discharged into 300 ml of water, and the solid is filtered off with suction and washed with water. After drying, 6.57 g of crude 2-amino-5-nitrobenzothiazole are obtained. The identity was confirmed by TLC comparison (TLC=thin-layer chromatography) with authentic material.

Workup

  1. temperatureis heated
  2. temperaturemaintained at this temperature for 1.5 hours
  3. filtrationthe solid is filtered off with suction
  4. washwashed with water
  5. customAfter drying

Sources & evidence

ORD record
ord-369eb3ee34054e6480240b0429e79ddf
Source dataset
uspto-grants-1989_02
Patent number
US04808723

Reaction notes

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