Ammonia → 148550-96-3

HRID 1708215Notes

Reaction equation

HRID 1708215 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:21]=[CH:20][C:8]2[S:9](=[O:19])[C:10]([C:16](O)=[O:17])=[C:11]([O:12][CH:13]([CH3:15])[CH3:14])[C:7]=2[CH:6]=1.S(Cl)(Cl)=O.[NH3:26].Cl>[Cl-].[Na+].O.C1COCC1.CN(C=O)C>[CH3:3][O:4][C:5]1[CH:21]=[CH:20][C:8]2[S:9](=[O:19])[C:10]([C:16]([NH2:26])=[O:17])=[C:11]([O:12][CH:13]([CH3:15])[CH3:14])[C:7]=2[CH:6]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 15959489HCID 15959489, compound

Product 1

HCID 5481003148550-96-3Yield 63%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium hydride (326 mg, 8.15 mmol) is washed free of oil and added to a room temperature solution of 5-methoxy-3-(1-methylethoxy)benzo[b]thiophene-2-carboxylic acid-1-oxide (2.30 g, 8.1 mmol) in a solvent system consisting of 25 mL of DMF and 75 mL of THF. After stirring at room temperature for 1.5 hours, the thick precipitate is cooled to -10° C. and thionyl chloride (713 μL, 9.78 mmol) is added. After 2 hours the solution is cooled to -78° C. resulting in the formation of a suspension. Ammonia gas is introduced under the surface for about 1 minute. After 10 minutes the reaction mixture is poured into a mixture of 6N HCl and brine. The organic phase is washed with additional acidic brine followed by saturated NaHCO3, then brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo. The resulting solid is recrystallized from EtOAc:hexane to provide 1.44 g (63%) of 5-methoxy-3-(1-methylethoxy)benzo[b]thiophene-2-carboxamide-1-oxide; mp 168.5°-169.5° C.

Workup

  1. temperaturethe thick precipitate is cooled to -10° C.
  2. temperatureAfter 2 hours the solution is cooled to -78° C.
  3. customresulting in the formation of a suspension
  4. washThe organic phase is washed with additional acidic brine
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting solid is recrystallized from EtOAc

Sources & evidence

ORD record
ord-c18b6c49546a4ed1a19d74d78dd901fd
Source dataset
uspto-grants-1994_10
Patent number
US05356926

Reaction notes

Loading…