Oxalyl chloride → 5-Thiazolecarboxylic acid, 4-methyl-, ethyl ester

HRID 388821Notes

Reaction equation

HRID 388821 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[C:7]([OH:9])=[O:8].[C:10](Cl)(=O)[C:11](Cl)=O>C(Cl)Cl.CN(C=O)C>[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 2098054-Methylthiazole-5-carboxylic acid

Product 1

HCID 2986105-Thiazolecarboxylic acid, 4-methyl-, ethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-methylthiazole-5-carboxylic acid was dissolved in DCM, cooled to 0° C., added oxalyl chloride (7.6 ml, 88 mmol) and DMF (2 drops). Reaction mixture was stirred for 30 mins and DCM was removed on rotavapour. Residue was dissolved in MeOH at 0° C. and stirred for 30 mins at rt. MeOH was removed on rotavapour and crude was worked up (AcOEt/H2O) to obtain the title compound (4.1 g) as a white solid. 1H-NMR (δ ppm, CDCl3, 400 MHz): 8.83 (s, 1H), 4.35 (q, J 7.2, 2H), 2.78 (s, 3H), 1.37 (t, J 7.2, 3H).

Workup

  1. customReaction mixture
  2. customDCM was removed on rotavapour
  3. dissolutionResidue was dissolved in MeOH at 0° C.
  4. stirringstirred for 30 mins at rt
  5. customMeOH was removed on rotavapour and crude

Sources & evidence

ORD record
ord-33fbc738728e46069d2441eefef4fc06
Source dataset
uspto-grants-2013_02
Patent number
US08377970B2

Reaction notes

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