HCID 13922894, compound → HCID 13922895, compound

HRID 2232375Notes

Reaction equation

HRID 2232375 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][S:5][CH2:6][C:7]1[CH:19]=[CH:18][C:10]2[S:11][C:12]([S:14](=[O:17])(=[O:16])[NH2:15])=[CH:13][C:9]=2[CH:8]=1.I([O-])(=O)(=O)=[O:22].[Na+]>C(O)C.O>[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][S:5]([CH2:6][C:7]1[CH:19]=[CH:18][C:10]2[S:11][C:12]([S:14](=[O:17])(=[O:16])[NH2:15])=[CH:13][C:9]=2[CH:8]=1)=[O:22]

Participants

5

Reactant 2

HCID 13922894HCID 13922894, compoundHCID 23667635Sodium periodate

Product 1

HCID 13922895HCID 13922895, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a partial solution of 5-[2-(dimethylamino)ethylthiomethyl]-2-sulfamoylbenzo[b]thiophene (1.32 g, 0.004 mol) in 20 ml of ethanol and 40 ml of water was added sodium metaperiodate (0.94 g, 0.0044 mol) and the mixture was stirred at room temperature for 16 hours over night. The reaction mixture was filtered and the filtrate was evaporated to dryness in vacuo. The white solid residue was recrystallized twice from 4/1 (V/V) water/ethanol and chromatographed on silica gel eluting with 7.5% (V/V) methanol/CHCl3. There was recovered 0.88 g of white solid, m.p. 180°-183° C., dec. (Yield 64%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated to dryness in vacuo
  3. customThe white solid residue was recrystallized twice from 4/1 (V/V) water/ethanol
  4. customchromatographed on silica gel eluting with 7.5% (V/V) methanol/CHCl3
  5. customThere was recovered 0.88 g of white solid, m.p. 180°-183° C., dec. (Yield 64%)

Sources & evidence

ORD record
ord-4e4cf2d3df9445168e2a1284793c9769
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

Loading…