Hydrazine → 1,3-Benzothiazole-2-carbohydrazide

HRID 409746Notes

Reaction equation

HRID 409746 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([O:12]CC)=O.[NH2:15][NH2:16]>C(O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([NH:15][NH2:16])=[O:12]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 640708Ethyl 1,3-benzothiazole-2-carboxylate

Product 1

HCID 3514191,3-Benzothiazole-2-carbohydrazideYield 99.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl benzo[d]thiazole-2-carboxylate (10 g, 48.25 mmol) in ethanol (200 mL) was added hydrazine (15.5 g, 482.5 mmol). The reaction mixture was stirred at RT for 30 min and concentrated under high vacuum to remove hydrazine. The resulting residue was triturated with ethanol (40 mL) to give benzo[d]thiazole-2-carbohydrazide (9.3 g, quant.) LRMS (M+H+) m/z 194.0.

Workup

  1. concentrationconcentrated under high vacuum
  2. customto remove hydrazine
  3. customThe resulting residue was triturated with ethanol (40 mL)

Sources & evidence

ORD record
ord-a196f37b208041ffbe3d2dc7dad0309c
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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