Potassium Carbonate → HCID 47171305, compound

HRID 472453Notes

Reaction equation

HRID 472453 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[N+:13]([C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18]Cl)([O-:15])=[O:14]>O>[CH3:7][N:8]([CH2:18][C:17]1[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=1[N+:13]([O-:15])=[O:14])[S:9]([CH3:12])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119212-Nitrobenzyl chlorideHCID 97632N-Methylmethanesulfonamide

Product 1

HCID 47171305HCID 47171305, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of potassium carbonate (1.2 g, 8.7 mmol) in was added N-methyl-methanesulfonamide (0.70 g, 6.4 mmol) followed by o-nitrobenzylchloride (1.0 g, 5.8 mmol). The mixture was heated at 50° C. for 18 hours. The mixture was cooled to room temperature and diluted with water (50 mL) and stirred for 30 minutes. The resulting precipitate was filtered and rinsed with water. The solid was dissolved in dichloromethane (25 mL), dried over magnesium sulfate, filtered, evaporated under reduced pressure then placed under high vacuum for 2 hours. N-Methyl-N-(2-nitro-benzyl)-methanesulfonamide was isolated as an orange-brown solid (1.12 g, 78%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.07 (d, J=8.0 Hz, 1H), 7.82 (d, J=7.9 Hz, 1H), 7.70 (t, J=7.4 Hz, 1H), 7.49 (t, J=7.7 Hz, 1H), 4.73 (s, 2H), 2.96 (s, 3H), 2.88 (s, 3H). MS=245 (MH)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. washrinsed with water
  4. dissolutionThe solid was dissolved in dichloromethane (25 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. waitthen placed under high vacuum for 2 hours

Sources & evidence

ORD record
ord-a646e35792a64aaab9eeb73af94047cd
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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