Methanesulfonyl chloride → 1-(4-Benzyloxy-3-methanesulphonamidophenyl)ethanone

HRID 964620Notes

Reaction equation

HRID 964620 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][C:10]=2[NH2:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1>[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][C:10]=2[NH:18][S:20]([CH3:19])(=[O:22])=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 155794401-[3-Amino-4-(benzyloxy)phenyl]ethan-1-one

Product 1

HCID 123639231-(4-Benzyloxy-3-methanesulphonamidophenyl)ethanoneYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mechanically stirred 16° C. pyridine (270 mL) solution of 1-[4-phenylmethoxy-3-aminophenyl]ethanone (57.4 g, 238 mmol) under N2, was added methanesulfonyl chloride (18.6 mL, 240 mmol). After 39 minutes, the completed reaction was quenched with 1.8 L H2O and the resulting suspension stirred for ~2 hours before filtration. The collected solids were washed with H2O (2×250 mL=500 mL) and partially air dried. These solids were dissolved in CHCl3 (450 mL), the aqueous phase removed and heptane (475 mL) added with stirring. The resulting fine suspension was filtered after ~15 minutes, washed with hexane and dried in vacuo at 55° C. to give 59 g (78%) of the title compound.

Workup

  1. customthe completed reaction
  2. customwas quenched with 1.8 L H2O
  3. washThe collected solids were washed with H2O (2×250 mL=500 mL) and partially air
  4. customdried
  5. dissolutionThese solids were dissolved in CHCl3 (450 mL)
  6. customthe aqueous phase removed
  7. additionheptane (475 mL) added
  8. stirringwith stirring
  9. filtrationThe resulting fine suspension was filtered after ~15 minutes
  10. washwashed with hexane
  11. customdried in vacuo at 55° C.

Sources & evidence

ORD record
ord-8f4e7c1944954e5bb24d49dcdd2a6781
Source dataset
uspto-grants-1998_06
Patent number
US05770615

Reaction notes

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