Methylamine → N-Methyl-4-nitrobenzeneethanesulfonamide

HRID 1508078Notes

Reaction equation

HRID 1508078 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][S:12]([N:15]2CCOC[CH2:16]2)(=[O:14])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].CN>CO>[CH3:16][NH:15][S:12]([CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 589943904-[2-(4-Nitro-phenyl)-ethanesulfonyl]-morpholine

Product 1

HCID 13475730N-Methyl-4-nitrobenzeneethanesulfonamideYield 19.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 2.12 g (8.49 mmol) of 2-(4-nitro-phenyl)-ethanesulfonyl chloride (as prepared in Example 26, step (c)) in MeOH (40 mL) was cooled to 0° C. and treated with 21.2 mL (42.4 mmol) of methylamine (2.0 M in MeOH). The mixture was slowly warmed to RT, stirred for 16 h, and warmed to 40° C. for 3 days. Solvents were evaporated in vacuo. Silica gel chromatography of the residue on a 50-g Varian MegaBond Elut SPE column with 50% EtOAc-hexane afforded 402 mg (19%) of the title compound as a white solid: 1H-NMR (CD3CN; 400 MHz): δ 8.19 (d, 2H, J=8.8 Hz), 7.54 (d, 2H, J=8.8 Hz), 5.15-5.05 (br s, 1H), 3.39-3.32 (m, 2H), 3.22-3.15 (m, 2H), 2.70 (d, 3H, J=5.2 Hz).

Workup

  1. temperatureThe mixture was slowly warmed to RT
  2. temperaturewarmed to 40° C. for 3 days
  3. customSolvents were evaporated in vacuo

Sources & evidence

ORD record
ord-1dee38c34f154eeea3bb9547d84f862a
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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