Triethylamine → 1-(Methylsulphonylaminocarbonyl)-3-nitrobenzene

HRID 2399683Notes

Reaction equation

HRID 2399683 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].C(N(CC)CC)C.[N+:13]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=[O:20])([O-:15])=[O:14]>ClCCl>[CH3:1][S:2]([NH:5][C:19]([C:18]1[CH:22]=[CH:23][CH:24]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=1)=[O:20])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 72879Methanesulfonamide

Product 1

HCID 196035271-(Methylsulphonylaminocarbonyl)-3-nitrobenzeneYield 32.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of methylsulphonamide (5.37 g, 57 mmol) in anhydrous dichloromethane (100 ml), cooled to 0° C. was treated with triethylamine (7.9 ml, 57 mmol) followed by a solution of 3-nitrobenzoyl chloride (10 g, 54 mmol) in anhydrous dichloromethane (100 ml) dropwise. After stirring for 2 h at 0° C., the reaction mixture was washed with 1M HCl (100 ml). The precipitate which formed was collected by filtration and triturated with diethyl ether and was then recrystallised from hot methanol to afford the title compound (4.3 g, 31%) as a colourless crystalline solid, mp 175°-178° C. 1H NMR (360 MHz, D6 -DMSO) δ 3.42 (3H, s), 7.82 (1H, dd, J=8.0 and 8.0 Hz), 8.38 (1H, d, J=8.0 Hz), 8.49 (1H, d, J=8.0 Hz), 8.80 (1H, s).

Workup

  1. washthe reaction mixture was washed with 1M HCl (100 ml)
  2. customThe precipitate which formed
  3. filtrationwas collected by filtration
  4. customtriturated with diethyl ether
  5. customwas then recrystallised from hot methanol

Sources & evidence

ORD record
ord-36cb338005144b8ca5f20cf23008c044
Source dataset
uspto-grants-1995_09
Patent number
US05451582

Reaction notes

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