Methylamine → HCID 18714928, compound

HRID 1048980Notes

Reaction equation

HRID 1048980 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].CC([O-])=O.[Na+].[CH3:21][NH2:22]>CS(C)=O>[CH3:21][NH:22][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 517045Sodium AcetateHCID 1237829HCID 1237829, compound

Product 1

HCID 18714928HCID 18714928, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of N-(4-fluoro-3-nitrophenyl) methane sulfonamide (0.5 g, 0.0021 mol) in DMSO (10 ml) was added NaOAc (1.75 ml, 0.0021 mol) and methyl amine (0.65 g, 0.0021 mol) portion wise with constant stirring. The reaction mixture was allowed to stir at 120° C. for 10 h. The reaction mixture was concentrated and diluted with water (10 ml) and extracted with DCM (3×15 nil). The combined organic layers were washed with brine dried over Na2SO4 and concentrated in vacuo to afford the desired product N-(4-(methyl amino)-3-nitrophenyl)methane sulfonamide (21) as a red color solid. 1H NMR (400 MHz, DMSO-d6), δ: 9.4 (s, 1H), 8.16 (bs, 1H), 7.93 (s, 1H), 7.46-7.43 (dd, J=9.2 Hz, 2.4 Hz, 1H), 7.04-7.01 (d, J=9.2 Hz, 1H), 2.95-2.94 (d, J=4.8 Hz, 3H), 2.92 (s, 3H). LCMS (ES) m/e MS (M−1=244). Purity: 94%.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water (10 ml)
  3. extractionextracted with DCM (3×15 nil)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59293333ea5e4cbaa1bac25b4c3764c1
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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