Potassium Carbonate → HCID 47171305, compound
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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
171 a) 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)+. 171 b) N-(2-Amino-benzyl)-N-methyl-methanesulfonamide was prepared from N-methyl-N-(2-nitro-benzyl)-methanesulfonamide (1.12 g, 4.58 mmol) in a manner analogous to
Workup
- temperatureThe mixture was cooled to room temperature
- filtrationThe resulting precipitate was filtered
- washrinsed with water
- dissolutionThe solid was dissolved in dichloromethane (25 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated under reduced pressure
- waitthen placed under high vacuum for 2 hours
Sources & evidence
- ORD record
- ord-04ce505d71db4cab93d1fb8529bdcf14
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501936B2
Reaction notes
Loading…