HCID 13922894, compound → HCID 13922895, compound

HRID 979591Notes

Reaction equation

HRID 979591 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-a73a213dbb8841e4993028d2a0c9fbbc
Source dataset
uspto-grants-1987_05
Patent number
US04668697

Reaction notes

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