Potassium Carbonate → 2-[[2-chloro-5-(1-hydroxy-1-methyl-ethyl)-phenyl]-(3,4-dimethoxy-benzenesulfonyl)-amino]-N,N-diethyl-acetamide

HRID 1674663Notes

Reaction equation

HRID 1674663 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)(=[O:15])=[O:14].Cl[CH2:27][C:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[O:29].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[N:12]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)(=[O:15])=[O:14])[CH2:27][C:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[O:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16844Chloro-N,N-diethylacetamideHCID 57511302N-[2-chloro-5-(1-hydroxy-1-methyl-ethyl)-phenyl]-3,4-dimethoxy-benzenesulfonamide

Product 1

HCID 575113202-[[2-chloro-5-(1-hydroxy-1-methyl-ethyl)-phenyl]-(3,4-dimethoxy-benzenesulfonyl)-amino]-N,N-diethyl-acetamideYield 92.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-[2-chloro-5-(1-hydroxy-1-methyl-ethyl)-phenyl]-3,4-dimethoxy-benzenesulfonamide (0.98 g, 2.5 mmol) in DMF (7.5 mL) was added 2-Chloro-N,N-diethyl-acetamide (0.418 g, 1.1 eq) and K2CO3 (0.35 g, 1 eq). The mixture was heated at 80° C. over night, cooled and partitioned between EA and water. The organic layer was washed several times with water and brine, dried over MgSO4 and concentrated. The residue was purified by chromatography on SiO2 (hex/EA 1:1, EA) to give the product as a colourless foam (1.15 g, 92%).

Workup

  1. temperaturecooled
  2. custompartitioned between EA and water
  3. washThe organic layer was washed several times with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on SiO2 (hex/EA 1:1, EA)

Sources & evidence

ORD record
ord-ddbd9bd5544d417e9835f05fae42b64f
Source dataset
uspto-grants-2011_08
Patent number
US08003654B2

Reaction notes

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