p-Fluoronitrobenzene → 2-(4-Nitrophenyl)-[1,2]thiazinane-1,1-dioxide

HRID 1434532Notes

Reaction equation

HRID 1434532 reaction equation
[S:1]1(=[O:8])(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][NH:2]1.[H-].[Na+].F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>CN(C=O)C>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([N:2]2[CH2:3][CH2:4][CH2:5][CH2:6][S:1]2(=[O:8])=[O:7])=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 3035081,4-Butanesultam

Product 1

HCID 690668132-(4-Nitrophenyl)-[1,2]thiazinane-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

500 mg (3.7 mmol) [1,2]thiazinane-1,1-dioxide, dissolved in 10 ml DMF, are added to a suspension of 163 mg sodium hydride dispersion in mineral oil (60%, 4.07 mmol) in 5 ml DMF. The mixture is stirred for 15 minutes, then a solution of 522 mg (3.7 mmol) 1-fluoro-4-nitrobenzene in 10 ml DMF is added dropwise. After two hours the reaction mixture is poured onto ice water. The solid is filtered off, washed with water and dried.

Workup

  1. additionAfter two hours the reaction mixture is poured onto ice water
  2. filtrationThe solid is filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-7d724c62a2344f4ca332a21c8b1a3f9a
Source dataset
uspto-grants-2009_11
Patent number
US07615549B2

Reaction notes

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