Sodium Nitrate → N-butyl-N-(6-nitro-1,1-dioxo-2,3-dihydro-1H-benzo[b]thiophen-3-yl)-methanesulfonamide

HRID 850023Notes

Reaction equation

HRID 850023 reaction equation
[CH2:1]([N:5]([CH:10]1[CH2:14][S:13](=[O:16])(=[O:15])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]1=2)[S:6]([CH3:9])(=[O:8])=[O:7])[CH2:2][CH2:3][CH3:4].[N+:21]([O-])([O-:23])=[O:22].[Na+]>S(=O)(=O)(O)O>[CH2:1]([N:5]([CH:10]1[CH2:14][S:13](=[O:15])(=[O:16])[C:12]2[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:11]1=2)[S:6]([CH3:9])(=[O:7])=[O:8])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 9926984N-butyl-N-(1,1-dioxo-2,3-dihydro-1H-benzo[b]thiophen-3-yl)methanesulfonamide

Product 1

HCID 9907002N-butyl-N-(6-nitro-1,1-dioxo-2,3-dihydro-1H-benzo[b]thiophen-3-yl)-methanesulfonamideYield 86.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

At -10° C., 0.5 g (1.6 mmol) of N-butyl-N-(1,1-dioxo-2,3-dihydro-1H-benzo[b]thiophen-3-yl)methanesulfonamide (Example 5) was dissolved in 5 ml of concentrated sulfuric acid and admixed with 0.15 g (1.8 mmol) of sodium nitrate, and the mixture was stirred at RT for 20 h. The reaction mixture was poured into 50 ml of ice-water, stirred for 30 minutes, filtered off with suction, washed neutral with water and dried under reduced pressure. This procedure gave 0.5 g of N-butyl-N-(6-nitro-1,1-dioxo-2,3-dihydro-1H-benzo[b]thiophen-3-yl)-methanesulfonamide; m.p. 52-55° C.

Workup

  1. stirringstirred for 30 minutes
  2. filtrationfiltered off with suction
  3. washwashed neutral with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-726b243e501044668cbd50211f094fb0
Source dataset
uspto-grants-2000_01
Patent number
US06015822

Reaction notes

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