Methyl Bromide → HCID 22164290, compound

HRID 236680Notes

Reaction equation

HRID 236680 reaction equation
[CH3:1][C:2]([NH:10][S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Na+].[Na].[CH3:23]Br>CN(C)C=O>[CH3:23][N:10]([C:2]([CH3:1])([CH3:9])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:12])=[O:13]

Participants

6

Reactant 4

HCID 6323Methyl BromideHCID 24758Sodium hydrideHCID 3856345HCID 3856345, compound2×HCID 5360545Sodium

Product 1

HCID 22164290HCID 22164290, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

27.5 g (0.1 mole) of N-(α,α-dimethylbenzyl) benzenesulfonamide was added to 5.8 g (0.12 mole) of 50% sodium hydride in 200 ml of dry N,N-dimethyl formamide. The mixture was stirred at room temperature for 30 minutes to react them. To the resulting sodium salt of N-(α,α-dimethylbenzyl)benzenesulfonamide was added 16.1 g (0.17 mole) of methyl bromide. The mixture was heated to 60° C. and stirred for 1 hour. The N,N-dimethyl formamide was distilled off under reduced pressure, and cold water was added. The resulting white solid was recrystallized from methanol to afford N-methyl-N-(α,α-dimethylbenzyl)benzenesulfonamide in a yield of 87%. This compound is designated as compound No. 64 in Table 2 below, and its melting point and elemental analysis values are shown in Table 2.

Workup

  1. customto react them
  2. temperatureThe mixture was heated to 60° C.
  3. stirringstirred for 1 hour
  4. distillationThe N,N-dimethyl formamide was distilled off under reduced pressure, and cold water
  5. additionwas added
  6. customThe resulting white solid was recrystallized from methanol

Sources & evidence

ORD record
ord-8180531b25ef48c1815469734ceb273d
Source dataset
uspto-grants-1979_06
Patent number
US04157257

Reaction notes

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