Thionyl Chloride → 4-Bromothiazole-2-carbohydrazide

HRID 2170911Notes

Reaction equation

HRID 2170911 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:7]([OH:9])=O)[S:5][CH:6]=1.O=S(Cl)Cl.O.[NH2:15][NH2:16]>CO>[Br:1][C:2]1[N:3]=[C:4]([C:7]([NH:15][NH2:16])=[O:9])[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 24654Hydrazine hydrate (1:1)HCID 151220654-Bromo-1,3-thiazole-2-carboxylic acid

Product 1

HCID 580356604-Bromothiazole-2-carbohydrazideYield 78.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the 4-bromothiazole-2-carboxylic acid (2.0 g, 9.8 mmol) in MeOH (10 mL) was added SOCl2 (710 μL, 9.8 mmol) and the reaction was refluxed for 3 hours. The reaction was concentrated, the residue was suspended in EtOH (10 mL), hydrazine hydrate (2.4 mL, 49 mmol) was added and the reaction was heated to reflux for 90 minutes. The reaction was concentrated, suspended in CH3CN, filtered, and the solids were washed with CH3CN, Et2O, and dried to afford 1.7 g (77%) of 4-bromothiazole-2-carbohydrazide as a yellow solid. M+1=222.1

Workup

  1. temperaturethe reaction was refluxed for 3 hours
  2. concentrationThe reaction was concentrated
  3. temperaturethe reaction was heated
  4. temperatureto reflux for 90 minutes
  5. concentrationThe reaction was concentrated
  6. filtrationfiltered
  7. washthe solids were washed with CH3CN, Et2O
  8. customdried

Sources & evidence

ORD record
ord-0a18f912c896420fa0b5841ba0777e66
Source dataset
uspto-grants-2015_06
Patent number
US09051313B2

Reaction notes

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