Methanesulfonamide → HCID 66634153, compound

HRID 2359924Notes

Reaction equation

HRID 2359924 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:7]([OH:9])=O)[S:5][CH:6]=1.[CH3:10][S:11]([NH2:14])(=[O:13])=[O:12].N12CCCN=C1CCCCC2>O1CCCC1>[Br:1][C:2]1[N:3]=[C:4]([C:7]([NH:14][S:11]([CH3:10])(=[O:13])=[O:12])=[O:9])[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 151220654-Bromo-1,3-thiazole-2-carboxylic acid

Product 1

HCID 66634153HCID 66634153, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Bromo-1,3-thiazole-2-carboxylic acid (1.0 g, 4.8 mmol) were initially charged in tetrahydrofuran (10 ml). N,N′-Carbonyldiimidazole (1.17 g, 7.2 mmol) was added and the reaction mixture was heated under reflux for 1 h. Methanesulphonamide (0.69 g, 7.2 mmol) was added and, after 10 min, 1,8-diazabicyclo[5.4.0]undec-7-ene (1.10 g, 7.2 mmol). The reaction mixture was stirred at room temperature for 16 h and then the solvent was removed under reduced pressure. The residue was taken up in water and acidified with hydrochloric acid. The precipitated product was filtered off with suction. This gave 1.18 g (84% of theory) of 4-bromo-N-(methylsulphonyl)-1,3-thiazole-2-carboxamide.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 1 h
  3. customthe solvent was removed under reduced pressure
  4. filtrationThe precipitated product was filtered off with suction

Sources & evidence

ORD record
ord-0f645b2fd7de41bb8fcdc72664d68022
Source dataset
uspto-grants-2014_04
Patent number
US08686004B2

Reaction notes

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