Thionyl Chloride → 5-Bromofuran-2-carbohydrazide

HRID 386403Notes

Reaction equation

HRID 386403 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.BrC1OC(C(Cl)=O)=CC=1.O.[NH2:24][NH2:25]>O>[Br:1][C:2]1[O:6][C:5]([C:7]([NH:24][NH2:25])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 24654Hydrazine hydrate (1:1)HCID 685115-Bromo-2-furanecarboxylic acidHCID 27570115-Bromofuran-2-carbonyl chloride

Product 1

HCID 4686365-Bromofuran-2-carbohydrazide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5-bromo-furan-2-carboxylic acid (38.2 g, 200 mmol) and thionylchloride (163.1 g, 1.37 mol) was stirred at 70° C. overnight. The mixture of 5-bromo-furan-2-carbonyl chloride was evaporated, solved in tetrahydrofuran (10 ml) and added to a mixture of hydrazine monohydrate (120.1 g, 2.4 mol), followed by stirring for 0.5 hours at <5° C. Water (50 ml) was added followed by filtration. The crystalline product was recrystallized from ethanol (125 ml, 96%). Yield 21.2 g (52%).

Workup

  1. customwas evaporated
  2. stirringby stirring for 0.5 hours at <5° C
  3. filtrationfollowed by filtration
  4. customThe crystalline product was recrystallized from ethanol (125 ml, 96%)

Sources & evidence

ORD record
ord-2f6b5d70394a4929a29fc8f00d8ab132
Source dataset
uspto-grants-2013_02
Patent number
US08372832B2

Reaction notes

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