Methanesulfonyl chloride → HCID 18184523, compound

HRID 1358474Notes

Reaction equation

HRID 1358474 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][NH:15][C:16](=[O:28])[CH2:17][C:18]2[CH:23]=[C:22]([Br:24])[C:21]([O:25][CH3:26])=[C:20]([Br:27])[CH:19]=2)[CH:10]=[CH:11][CH:12]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:24][C:22]1[CH:23]=[C:18]([CH2:17][C:16]([NH:15][CH2:14][CH2:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH:8]=2)=[O:28])[CH:19]=[C:20]([Br:27])[C:21]=1[O:25][CH3:26]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 18184548HCID 18184548, compound

Product 1

HCID 18184523HCID 18184523, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (0.0313 g, 0.000273 mol) was added to DMAP (0.0334 g, 0.000273 mol) in methylene chloride (6 mL). To the resulting white complex N-[2-(3-amino-phenyl)-ethyl]-2-(3,5-dibromo-4-methoxy-phenyl)-acetamide (0.1 g, 0.000226 mol) in methylene chloride (6mL) was added dropwise. The reaction mixture was stirred for 18 h at room temperature, washed with 1 N HCl and 1 N NaOH. The organic layer was dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (silica gel, 1:1 ethyl acetate-hexane mixture). Yield 0.058 g, 49%. MS m/e 518.7 [M+H].

Workup

  1. washwashed with 1 N HCl and 1 N NaOH
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. custompurified by column chromatography (silica gel, 1:1 ethyl acetate-hexane mixture)

Sources & evidence

ORD record
ord-5a6e879569c54b0abb93c5cb0117f81e
Source dataset
uspto-grants-2003_07
Patent number
US06596734B1

Reaction notes

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