Methanesulfonyl chloride → HCID 67070011, compound

HRID 2390826Notes

Reaction equation

HRID 2390826 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:5]([O:17][CH3:18])=[C:6]([CH:16]=1)[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:5]([O:17][CH3:18])=[C:6]([CH:16]=1)[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][S:24]([CH3:23])(=[O:26])=[O:25])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 67070111HCID 67070111, compound

Product 1

HCID 67070011HCID 67070011, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

step 4—To a solution of 118 (0.20 g, 0.55 mmol) in pyridine (3 mL) cooled to 0° C. was added methanesulfonyl chloride (0.081 g, 0.71 mmol). Stirring was continued at 0° C. for 30 min then at RT for 3 h. The reaction mixture was diluted with EtOAc, washed sequentially with aqueous CuSO4 and 2N HCl, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with EtOAc/hexane to afford 0.20 g (84%) of N-[4-(5-bromo-3-tert-butyl-2-methoxybenzyloxy)phenyl]methanesulfonamide (120) as a white solid.

Workup

  1. waitat RT for 3 h
  2. washwashed sequentially with aqueous CuSO4 and 2N HCl
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by SiO2 chromatography
  7. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-093d335360524ae5b02f9aa9a912c92f
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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