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

HRID 1383054Notes

Reaction equation

HRID 1383054 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>S1(CCCC1)(=O)=O>[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-amine

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

A suspension of 10.13 g of 2,4-dinitrochlorobenzene and 15.2 g of thiourea in 50 ml of sulpholane (tetrahydrothiophene 1,1-dioxide) is stirred at 110° to 120° C. for 12 hours. After cooling, the mixture is thoroughly stirred with 800 ml of water, and the solid is filtered off with suction and washed with water. After drying, 11.2 g of a yellow powder which, according to HPLC analysis (high pressure liquid chromatography), contains 69.5% of 2-amino-5-nitrobenzothiazole (corresponding to 80% of theory) are obtained. Recrystallisation from dimethylformamide raises the melting point to 307° C. (decomposition) (Zhur. Obschei Khim. 30, 1363-6 (1960) reports melting point 308°-309° C., decomposition).

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid is filtered off with suction
  3. washwashed with water
  4. customAfter drying
  5. customare obtained
  6. customRecrystallisation from dimethylformamide
  7. temperatureraises the melting point to 307° C. (decomposition) (Zhur

Sources & evidence

ORD record
ord-1d0b1d475d97475db4fb3ede57137b88
Source dataset
uspto-grants-1989_02
Patent number
US04808723

Reaction notes

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