Dichloromethane → N-(4-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-methanesulfonamide

HRID 2354254

Reaction equation

HRID 2354254 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[CH:26]=[CH:25][C:16]([O:17][CH2:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:15]([CH3:27])[CH:14]=2)([CH2:11][CH3:12])[CH2:9][CH3:10])=[CH:4][C:3]=1[CH3:28].C(N(CC)CC)C.C(Cl)Cl.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C(Cl)Cl.ClCCl>[CH3:21][C:20]([CH3:22])([CH3:23])[C:19](=[O:24])[CH2:18][O:17][C:16]1[CH:25]=[CH:26][C:13]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:40]([CH3:39])(=[O:42])=[O:41])=[C:3]([CH3:28])[CH:4]=2)([CH2:11][CH3:12])[CH2:9][CH3:10])=[CH:14][C:15]=1[CH3:27]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 684529431-{4-[1-(4-Amino-3-methyl-phenyl)-1-ethyl-propyl]-2-methyl-phenoxy}-3,3-dimethyl-butan-2-one

Product 1

HCID 11224956N-(4-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-methanesulfonamideYield 87%

Reagents, catalysts & solvents 1

HCID 21925356DCM DichloromethaneSolvent

Procedure

To a 0° C. mixture of 1-{4-[1-(4-amino-3-methyl-phenyl)-1-ethyl-propyl]-2-methyl-phenoxy}-3,3-dimethyl-butan-2-one (763 mg, 2 mmol), triethylamine (0.42 mL, 3 mmol) and CH2Cl2 (7 mL) is added methanesulfonyl chloride (0.155 mL, 2 mmol). The reaction is warmed to RT and stirred for 3 h. The reaction is diluted with CH2Cl2 dichloromethane and washed with 0.2 N HCl. The organic phase is Na2SO4 dried, concentrated, and chromatogrpahed (0% to 25% EtOAc/Hex) to give the title compound (800 mg, 87%).

Workup

  1. washwashed with 0.2 N HCl
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a3803b1f1ab149ebacb58a4a7f69b14e
Source dataset
uspto-grants-2010_07
Patent number
US07750184B2

Linked notes

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