Hydrazine hydrate (1:1) → N-(2-chloro-5-fluorobenzyl)hydrazinecarbothioamide

HRID 240289Notes

Reaction equation

HRID 240289 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[CH2:12][N:13]=[C:14]=[S:15]>O1CCOCC1>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[CH2:12][NH:13][C:14]([NH:2][NH2:3])=[S:15]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866548531-Chloro-4-fluoro-2-(isothiocyanatomethyl)benzene

Product 1

HCID 86654854N-(2-chloro-5-fluorobenzyl)hydrazinecarbothioamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of hydrazine hydrate (80%, 13.4 g, 214 mmol) in 1,4-dioxane (100 mL) at 0° C. was added a solution of 1-chloro-4-fluoro-2-(isothiocyanatomethyl)benzene (26, 14.4 g, 71.6 mmol) in 1,4-dioxane (50 mL) The mixture was stirred at RT for 2 h. Ice cold water (300 mL) was added. The precipitated solid was collected by filtration, washed with water and dried over P2O5 overnight to provide N-(2-chloro-5-fluorobenzyl)hydrazinecarbothioamide (27). MS: m/z, 234 (100%, M+1), 236 (33%).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with water
  3. dry with materialdried over P2O5 overnight

Sources & evidence

ORD record
ord-3e43a443b64c4c41b4491fb7a534ed93
Source dataset
uspto-grants-2014_02
Patent number
US08648073B2

Reaction notes

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