Sodium Bicarbonate → L-691121

HRID 1781383Notes

Reaction equation

HRID 1781383 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]([CH:12]=1)=[N:9][O:10][N:11]=2.[ClH:13].[CH3:14][S:15]([NH:18][C:19]1[CH:20]=[CH:21][C:22]2[O:32][C:26]3([CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[CH2:25][C:24](=[O:33])[C:23]=2[CH:34]=1)(=[O:17])=[O:16].C(=O)(O)[O-].[Na+]>C(O)C>[ClH:13].[N:11]1[O:10][N:9]=[C:8]2[CH:12]=[C:4]([CH2:3][CH2:2][N:29]3[CH2:30][CH2:31][C:26]4([CH2:25][C:24](=[O:33])[C:23]5[CH:34]=[C:19]([NH:18][S:15]([CH3:14])(=[O:16])=[O:17])[CH:20]=[CH:21][C:22]=5[O:32]4)[CH2:27][CH2:28]3)[CH:5]=[CH:6][C:7]=12

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 117758995-(2-Bromoethyl)benzofurazanHCID 19045253N-(4-Oxospiro[chroman-2,4'-piperidine]-6-yl)methanesulfonamide hydrochloride

Product 1

HCID 164390L-691121Yield 41.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 5-(2-bromoethyl)benzofurazan (0.39 g, 1.72 mmol), 3,4-dihydro-6-methanesulfonamidospiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one hydrochloride (0.24 g, 0.69 mmol) and sodium bicarbonate (0.21 g, 2.55 mmol) in ethanol (13.2 ml) was heated at reflux temperature for 24 hr. Solvent evaporation and chromatography (silica gel, chloroform-methanol-ammonium hydroxide, 97/3/0.3) gave an oil; conversion to the hydrochloride gave the hydrochloride (0.14 g, 41%); mp>250° C. Anal. Calcd for C22H24N4O3 ·HCl C, 53.59; H, 5.12, N, 11.37. Found: C, 53.55; H, 5.15; N, 11.12.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 24 hr
  3. customSolvent evaporation and chromatography (silica gel, chloroform-methanol-ammonium hydroxide, 97/3/0.3)
  4. customgave an oil

Sources & evidence

ORD record
ord-6d12d6442a96446d8a9c31f411e01809
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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