Methylamine → HCID 4830484, compound

HRID 2077512Notes

Reaction equation

HRID 2077512 reaction equation
[CH3:1][NH2:2].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11]>C(O)C.CCOC(C)=O.O>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:2][CH3:1])(=[O:12])=[O:11]

Participants

6

Reactant 2

HCID 6329MethylamineHCID 1377612-Fluorobenzenesulphonyl chloride

Product 1

HCID 4830484HCID 4830484, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A RBF was charged with methylamine (0.5 mL, 40%, 14 mmol) in ethanol (2 mL). The mixture was chilled to 0° C. in an ice bath while being stirred under an inert atmosphere. 2-Fluorobenzenesulfonyl chloride (0.6 mL, 3 mmol) was added dropwise into the mixture. The resulting mixture was allowed to stir at 0° C. for 30 minutes. The mixture was diluted with EtOAc and water. The aqueous layer was extracted with EtOAc three times, and the combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 2-fluoro-N-methylbenzenesulfonamide (0.530 g, 99% yield) as a colorless oil. MS (ESI pos. ion) m/z: 190 (MH+). Calculated exact mass for C7H8FNO2S: 189.

Workup

  1. stirringto stir at 0° C. for 30 minutes
  2. extractionThe aqueous layer was extracted with EtOAc three times
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ce1102ec7e34ce09c5addfd6d857442
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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