Thionyl Chloride → 4-Bromothiazole-2-carbohydrazide

HRID 1754274Notes

Reaction equation

HRID 1754274 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-carbohydrazide

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 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-7a1e2be7825a4e7aab52039a1b0115c1
Source dataset
uspto-grants-2015_10
Patent number
US09169243B2

Reaction notes

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