Water → (4-Chloro-benzothiazol-2-yl)-hydrazine

HRID 1578516Notes

Reaction equation

HRID 1578516 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([NH2:11])[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.O.[NH2:13]N.O>COCCOCCO>[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([NH:11][NH2:13])[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 298722-Benzothiazolamine, 4-chloro-

Product 1

HCID 2049837(4-Chloro-benzothiazol-2-yl)-hydrazineYield 78%

Reagents, catalysts & solvents 1

HCID 8134Diethylene Glycol Monomethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

4-Chloro-2-aminobenzothiazole (2.0 g.; 0.0108 mole) was dissolved in 10 milliliters of diethylene glycol monomethyl ether and 0.9 milliliter of concentrated HC1 added with stirring. 85% Hydrazine hydrate (1.92 g.) was then added to the mixture, and the reaction mixture was heated to 110°C., under N2 atmosphere, on an oil bath. The reaction was continued for 22 hours, the final reaction temperature being 120°C. The 4-chloro-2-hydrazinobenzothiazole product was isolated by addition of water and separated by filtration, 1.69 g. (78% yield), m.p. 232°-235°C.

Workup

  1. addition0.9 milliliter of concentrated HC1 added
  2. customthe final reaction temperature
  3. custombeing 120°C

Sources & evidence

ORD record
ord-355841bff0b041b0b2bae2d926ccff73
Source dataset
uspto-grants-1976_02
Patent number
US03937714

Reaction notes

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