Acetic Acid → 2-Hydrazinyl-4,6-dinitro-1,3-benzothiazole

HRID 1088207Notes

Reaction equation

HRID 1088207 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([N+:14]([O-:16])=[O:15])[C:5]=2[N:6]=1.O.[NH2:18]N.O.C(O)(=O)C>C(OCCO)C>[NH:1]([C:2]1[S:3][C:4]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([N+:14]([O-:16])=[O:15])[C:5]=2[N:6]=1)[NH2:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 139850824,6-Dinitro-1,3-benzothiazol-2-amine

Product 1

HCID 139850832-Hydrazinyl-4,6-dinitro-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

24.0 g of amino-4,6-dinitrobenzthiazole are heated to boiling for 1 hour in 200 ml of 2-ethoxyethanol with 20 ml of hydrazine hydrate (100% purity). After cooling to room temperature, the reaction mixture is poured into a mixture of 750 ml of water and 20 ml of glacial acetic acid, stirred for 1 hour, filtered off under suction, washed with water and dried. 21.0 g of 2-hydrazino-4,6-dinitrobenzthiazole are obtained. Melting point 210°-214° C. (decomposition). After recrystallization from 2-methoxyethanol. Melting point 216°-217° C. (decomposition).

Workup

  1. filtrationfiltered off under suction
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-05bfdc03b19248b5b83a449840a6eb88
Source dataset
uspto-grants-1990_10
Patent number
US04962040

Reaction notes

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