Methanesulfonyl chloride → HCID 86590466, compound

HRID 1062323Notes

Reaction equation

HRID 1062323 reaction equation
Br.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[N:7]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14]>C(Cl)Cl>[CH3:11][O:10][C:8]([C:6]1[N:7]=[C:3]([NH:2][S:13]([CH3:12])(=[O:15])=[O:14])[S:4][CH:5]=1)=[O:9]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 22286972HCID 22286972, compound

Product 1

HCID 86590466HCID 86590466, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a well stirred solution of methyl 2-amino-thiazole-4-carboxylate hydrobromide (Justus Liebigs Ann. Chem. 1951, 571, 44, Heterocycles 1997, 45, 1299) (13 g, 51 mmol) and TEA (40 mL, 290 mmol) in DCM (130 mL) at rt was added methanesulfonyl chloride (11 mL, 140 mmol) dropwise. After stirring for 1 h, the reaction mixture was filtered and the filtrate concentrated. The residue was re-suspended in ethyl acetate, filtered and chromatographed on silica gel (ethyl acetate/ethanol, 97:3) to provide 2-methanesulfonylamino-thiazole-4-carboxylic acid methyl ester (5.5 g). MS (ESI−) for C6H8N2O4S2 m/z 234.9 (M−H)−.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate concentrated
  3. filtrationfiltered
  4. customchromatographed on silica gel (ethyl acetate/ethanol, 97:3)

Sources & evidence

ORD record
ord-d9e8d63942444e7d918adc41c41c1ce9
Source dataset
uspto-grants-2005_11
Patent number
US06960664B2

Reaction notes

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