Sodium Chloride → HCID 18950741, compound

HRID 1492564Notes

Reaction equation

HRID 1492564 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:13][CH2:14][NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[CH:7][CH:6]=1.C([Li])CCC.[C:37](Cl)(=[O:41])[O:38][CH2:39][CH3:40].[Cl-].[Na+]>O1CCCC1.CCCCCC>[CH2:39]([O:38][C:37]([N:15]([CH2:14][CH2:13][CH:12]([C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)[CH2:11][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][CH:9]=1)[S:16]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)(=[O:17])=[O:18])=[O:41])[CH3:40]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 10928Ethyl chloroformateHCID 18950744HCID 18950744, compoundHCID 178418339Butyllithium

Product 1

HCID 18950741HCID 18950741, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

In argon atmosphere, 329 mg of N-[4-(4-methoxymethyloxyphenyl)-3-(3-pyridyl)butyl]-4-chlorobenzene sulfonamide was dissolved in 12 ml of dry tetrahydrofuran, and cooled to 0° C., followed by addition of 0.67 ml of the solution of 1.55M n-butyl lithium in hexane, which was then stirred for 30 minutes. At the same temperature, 116 mg of ethyl chlorocarbonate dissolved in 3 ml of dry tetrahydrofuran was added dropwise and stirred at room temperature for 24 hours. To the reaction mixture was added saturated aqueous sodium chloride, and the organic phase was separated which was then extracted with ethyl acetate. The organic phases combined were washed in saturated aqueous sodium chloride and dried over magnesium sulfate, so the solvent was distilled off under reduced pressure. The obtained residue was subjected to preparative silica gel TLC which was then developed with methanol-methylene chloride (4:96 v/v) to obtain 204 mg of N-ethoxycarbonyl-N-[4-(4-methoxymethyloxyphenyl)-3-(3-pyridyl)butyl]-4-chlorobenzene sulfonamide from a band of 0.36 to 0.53.

Workup

  1. additionwas added dropwise
  2. stirringstirred at room temperature for 24 hours
  3. customthe organic phase was separated which
  4. extractionwas then extracted with ethyl acetate
  5. washThe organic phases combined were washed in saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate, so the solvent
  7. distillationwas distilled off under reduced pressure

Sources & evidence

ORD record
ord-f869962524f84f14bbc9df72b415cda7
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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