Methanesulfonyl chloride → HCID 68741270, compound

HRID 2382595Notes

Reaction equation

HRID 2382595 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10](=[O:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C(Cl)Cl.N1C=CC=CC=1>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:9][C:10](=[O:12])[CH3:11])=[CH:3][C:2]=1[NH:1][S:14]([CH3:13])(=[O:16])=[O:15]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68724436HCID 68724436, compound2×

Product 1

HCID 68741270HCID 68741270, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-Amino-4-chloro-phenyl)-propan-2-one (Intermediate D) (0.5 g, 2.73 mmol) in DCM (2 ml) and pyridine (1 ml) is added drop wise methanesulfonyl chloride (0.34 g, 0.23 ml, 3.0 mmol) at 0° C. (ice-bath). The reaction mixture is allowed to warm to room temperature and stirred for 3 days. The solvents are removed in vacuo and the residue is dissolved in EtOAc and washed with water, the organic portion is dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica eluting with EtOAc affords the title compound.

Workup

  1. customThe solvents are removed in vacuo
  2. dissolutionthe residue is dissolved in EtOAc
  3. washwashed with water
  4. dry with materialthe organic portion is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the crude residue by flash chromatography on silica eluting with EtOAc

Sources & evidence

ORD record
ord-83a400f104a1459eb6803bbb0114e0bb
Source dataset
uspto-grants-2012_09
Patent number
US08263585B2

Reaction notes

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