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

HRID 524110Notes

Reaction equation

HRID 524110 reaction equation
O.[NH2:2][NH2:3].[Br: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>[Br: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 866548501-Bromo-4-fluoro-2-(isothiocyanatomethyl)benzene

Product 1

HCID 86654851N-(2-bromo-5-fluorobenzyl)hydrazinecarbothioamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of hydrazine hydrate (80%, 2.22 g, 35.5 mmol) in 1,4-dioxane (20 mL) at 0° C. was added a solution of 1-bromo-4-fluoro-2-(isothiocyanatomethyl)benzene (13, 3.16 g, 12.8 mmol) in 1,4-dioxane (5 mL) The mixture was stirred at RT for 2 h. Ice cold water (100 mL) was added. The precipitated solid was collected by filtration, washed with water, and dried over P2O5 overnight to provide N-(2-bromo-5-fluorobenzyl)hydrazinecarbothioamide (14). MS: m/z, 278 (100%, M+1), 280 (100%), 300 (10%, M+23), 302 (10%).

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-fecb073b0c604583b4b9ea1dad043bfb
Source dataset
uspto-grants-2016_05
Patent number
US09340523B2

Reaction notes

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