Oxalyl chloride → 4-(Propan-2-yl)-1,3-thiazole-2-carbonyl chloride

HRID 553439Notes

Reaction equation

HRID 553439 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH:7]([C:10]1[N:11]=C(C(O)=O)[S:13][CH:14]=1)([CH3:9])[CH3:8]>C1(C)C=CC=CC=1>[CH:7]([C:10]1[N:11]=[C:1]([C:2]([Cl:4])=[O:3])[S:13][CH:14]=1)([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 224993072-Thiazolecarboxylic acid, 4-(1-methylethyl)-

Product 1

HCID 575787964-(Propan-2-yl)-1,3-thiazole-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Oxalyl chloride (5.71 g, 45 mmol., 3.0 eq) was added dropwise, at ambient temperature, to a solution of 4-isopropyl-thiazole-2-carboxylic acid (3.85 g, 22.5 mmol., 1.5 eq) in toluene (40 mL). Stirring was continued at ambient temperature until the bubbling stopped. The reaction mixture was then heated under reflux for a further 1 hour. LCMS analysis of an aliquot quenched with methanol revealed full conversion of the acid to the acid chloride. The reaction mixture was left to cool to ambient temperature and the solvent removed under vacuum. The crude material was used directly in the next step without further purification.

Workup

  1. customwas continued at ambient temperature until the bubbling
  2. temperatureThe reaction mixture was then heated
  3. temperatureunder reflux for a further 1 hour
  4. customLCMS analysis of an aliquot quenched with methanol revealed full conversion of the acid to the acid chloride
  5. waitThe reaction mixture was left
  6. customthe solvent removed under vacuum
  7. customThe crude material was used directly in the next step without further purification

Sources & evidence

ORD record
ord-c0d4b3c6dc804cd2be2fa6f6e6652068
Source dataset
uspto-grants-2011_11
Patent number
US08048862B2

Reaction notes

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