Ammonia → HCID 70688908, compound

HRID 1092937Notes

Reaction equation

HRID 1092937 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[NH3:27].C(OCC)C>O1CCOCC1>[CH3:10][C:8]1[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=1[C:11]1[CH:16]=[CH:15][C:14]([S:17](=[O:19])(=[O:18])[NH2:27])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 85861720HCID 85861720, compound

Product 1

HCID 70688908HCID 70688908, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4-(2-Acetylamino-4-methyl-thiazol-5-yl)-benzenesulfonyl chloride (3a) (3.8 g, 11.5 mmol) is dissolved in dioxane (50 ml) with stirring. Sodium carbonate (2.45 g, 23 mmol) is added followed by a solution of ammonia in dioxane (50 ml, 0.75 M). After stirring for 2 hours at room temperature diethyl ether (120 ml) is added and the solid precipitate is removed by filtration. The solid is stirred in tetrahydrofuran (200 ml) and the mixture is then filtered through Celite™ filter material to remove inorganic material. Removal of the solvent affords N-[4-methyl-5-(4-sulfamoyl-phenyl)-thiazol-2-yl]-acetamide.

Workup

  1. additionis added
  2. customthe solid precipitate is removed by filtration
  3. stirringThe solid is stirred in tetrahydrofuran (200 ml)
  4. filtrationthe mixture is then filtered through Celite™
  5. filtrationfilter material
  6. customto remove inorganic material
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-cd0ef1d277754e65bbc50c8ecaeda436
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

Loading…