Benzenesulfonyl chloride → HCID 10367410, compound

HRID 1639129Notes

Reaction equation

HRID 1639129 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][O:8][C:7]2[CH:16]=[CH:17][C:18]([C:20]([O:22][CH3:23])=[O:21])=[CH:19][C:6]1=2.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>N1C=CC=CC=1>[C:24]1([S:30]([NH:1][CH2:2][CH2:3][S:4][CH:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH2:9][O:8][C:7]3[CH:16]=[CH:17][C:18]([C:20]([O:22][CH3:23])=[O:21])=[CH:19][C:6]2=3)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 14724118HCID 14724118, compound2×

Product 1

HCID 10367410HCID 10367410, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 100 ml of pyridine was dissolved 9.00 g of methyl 11-(2-aminoethyl)thio-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate (Compound f) obtained in Reference Example 6. Under ice cooling, 4.2 ml of benzenesulfonyl chloride was dropwise added to the solution and the mixture was stirred at room temperature overnight. Pieces of ice were added to the mixture. After stirring for further an hour, the solvent was distilled off under reduced pressure. The residue was extracted with 500 ml of ethyl acetate and the extract was washed in sequence with saturated sodium bicarbonate aqueous solution and then with saturated sodium chloride aqueous solution. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluting solvent; hexane:ethyl acetate=7:3) to give 9.90 g of the desired compound.

Workup

  1. customobtained in Reference Example 6
  2. additionPieces of ice were added to the mixture
  3. stirringAfter stirring for further an hour
  4. distillationthe solvent was distilled off under reduced pressure
  5. extractionThe residue was extracted with 500 ml of ethyl acetate
  6. washthe extract was washed in sequence with saturated sodium bicarbonate aqueous solution
  7. dry with materialAfter drying over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. washThe resulting residue was subjected to silica gel column chromatography (eluting solvent; hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-6b44349618674732aba602754cc73d91
Source dataset
uspto-grants-1989_11
Patent number
US04882351

Reaction notes

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