Methanesulfonamide → HCID 69103485, compound

HRID 2220367Notes

Reaction equation

HRID 2220367 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH:3]=1.[CH3:16][S:17]([NH2:20])(=[O:19])=[O:18].Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:20][S:17]([CH3:16])(=[O:19])=[O:18])=[O:7])=[C:4]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH:3]=1

Participants

7

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69102536HCID 69102536, compound

Product 1

HCID 69103485HCID 69103485, compoundYield 93.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

To a suspension of 4-bromo-2-(3-methylbutyl)benzoic acid (1.3 g) and methanesulfonamide (365 mg) in N,N-dimethylformamide (12 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (735 mg) and 4-dimethylaminopyridine (469 mg), and stirred at 30° C. for 16 hours. The mixture was diluted with ethyl acetate, washed with 1N aqueous hydrochloride solution, water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give 4-bromo-2-(3-methylbutyl)-N-(methylsulfonyl)benzamide (1.25 g).

Workup

  1. washwashed with 1N aqueous hydrochloride solution, water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-7cba264750b5416dbb03487ae38214ec
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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