Methanesulfonyl chloride → HCID 91178574, compound

HRID 271836Notes

Reaction equation

HRID 271836 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]1([C@H:12]([NH2:14])[CH3:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)Cl>[C:6]1([C@H:12]([NH:14][S:2]([CH:1]=[CH:13][C:12]2[C:6]3[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=3[N:14]([CH2:12][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:14]=2)(=[O:4])=[O:3])[CH3:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 6431891-Phenethylamine, (+)-

Product 1

HCID 91178574HCID 91178574, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride Compound 11f1 (2.0 g, 17 mMol) and TEA (2.43 mL, 17.46 mMol) were added to a solution of (1R)-1-phenyl-ethylamine Compound 11f2 (1.75 g, 17.5 mMol) in CH2Cl2 (50 mL) at 0° C. under a N2 atmosphere. The mixture was stirred for 3 hrs while warming to r.t., then the reaction was quenched with water (5 mL). The organic layer was diluted with CH2Cl2 (100 mL) and then washed with water and brine. The organic layer was separated, dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to afford the corresponding N-(1-phenyl-ethyl)-methanesulfonamide Compound 11f3 as an oil.

Workup

  1. customthe reaction was quenched with water (5 mL)
  2. additionThe organic layer was diluted with CH2Cl2 (100 mL)
  3. washwashed with water and brine
  4. customThe organic layer was separated
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-261eb0716c2b4bf39bb3b61aba7ea5b3
Source dataset
uspto-grants-2008_11
Patent number
US07452997B2

Reaction notes

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