Sodium Iodide → HCID 68567676, compound

HRID 747621Notes

Reaction equation

HRID 747621 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)(=[O:11])=[O:10])=[C:4]([C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])([OH:24])[CH3:23])[CH:3]=1.[CH:32]([NH:35]C(C)C)(C)[CH3:33].[Li].BrCC(N)=[O:43].[I-].[Na+]>C(OCC)C.CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)(=[O:10])=[O:11])[C:33](=[O:43])[CH2:32][NH2:35])=[C:4]([C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])([OH:24])[CH3:23])[CH:3]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 696322-Bromoacetamide2×HCID 45051747Lithium diisopropylamineHCID 68567453HCID 68567453, compound

Product 1

HCID 68567676HCID 68567676, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1.3 g of N-{4-chloro-2-[1-(2-chlorophenyl)-1-hydroxyethyl]phenyl}-3,4-dimethoxybenzenesulfonamide dissolved in diethyl ether are successively added, at −5° C., 1.3 ml of a 2M solution of lithium diisopropylamine in hexane, and 0.45 g of 2-bromoacetamide. After 18 hours at room temperature, 0.5 g of 2-bromoacetamide and 1.4 g of sodium iodide are successively added and the mixture is refluxed for 4 hours. The reaction medium is taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with a 95/5 (v/v) dichloromethane/methanol mixture to give 0.51 g of the expected product.

Workup

  1. additionare successively added, at −5° C.
  2. temperaturethe mixture is refluxed for 4 hours
  3. washwashed with water
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed on a column of silica gel
  7. washeluting with a 95/5 (v/v) dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-04828a79995c418b88ec5aa60c1cca0a
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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