Hydrazine hydrate (1:1) → ethyl 2-hydrazino-4-methyl-1,3-thiazole-5-carboxylate

HRID 2381785Notes

Reaction equation

HRID 2381785 reaction equation
Br[C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.O.[NH2:14][NH2:15]>O1CCCC1>[NH:14]([C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1)[NH2:15]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 748178ethyl 2-hydrazino-4-methyl-1,3-thiazole-5-carboxylateYield 137.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A To a stirred solution of ethyl 2-bromo-4-methylthiazole-5-carboxylate (10.00 g, 40.00 mmol) in tetrahydrofuran (125 mL), was added hydrazine monohydrate (6.01 g, 120.0 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, concentrated in vacuo to dryness. The residue was purified by column chromatography to afford ethyl 2-hydrazinyl-4-methylthiazole-5-carboxylate as a white solid (11.06 g, 91%): 1H NMR (300 MHz, DMSO-d6) δ 5.02 (s, 2H), 4.13 (q, J=6.0 Hz, 2H), 2.33 (s, 3H), 1.18 (t, J=6.0 Hz, 3H); MS (ES+) m/z 202.2 (M+1).

Workup

  1. concentrationconcentrated in vacuo to dryness
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3ca8f940d37c4c9b8e144676639a78c4
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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