Methyl iodide → n-[6-Benzyloxy-2,2-dimethylchroman-4-yl]-n-methylmethanesulfonamide

HRID 567067Notes

Reaction equation

HRID 567067 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][CH:12]2[NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28]I>CC(N(C)C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][CH:12]2[N:21]([CH3:28])[S:22]([CH3:25])(=[O:23])=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 212645206-Benzyloxy-4-(methylsulfonyl)amino-2,2-dimethylchroman

Product 1

HCID 21264508n-[6-Benzyloxy-2,2-dimethylchroman-4-yl]-n-methylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

8.9 g (25 mmol) of 6-benzyloxy-4-(methylsulfonyl)amino-2,2-dimethylchroman (Ex. 1 e) were introduced in portions at 10° C. into a suspension of 1.2 g (30 mmol) of sodium hydride (60 percent dispersion) in 75 ml of DMA. After stirring at RT for 2 h, 1.9 ml (30 mmol) of methyl iodide were added dropwise, the temperature rising to 50° C. The mixture was then heated to 50° C. for 2 h, concentrated in vac., the residue was treated with water, the resinous product was taken up with EA, the solution was dried and concentrated, and the residue was chromatographed on silica gel using n-heptane/EA (2:1). 7.4 g of product were crystallized from appropriate fractions using petroleum ethendusopropyl ether (1:1), m.p. 114-116° C.

Workup

  1. customrising to 50° C
  2. temperatureThe mixture was then heated to 50° C. for 2 h
  3. concentrationconcentrated in vac
  4. addition, the residue was treated with water
  5. customthe solution was dried
  6. concentrationconcentrated
  7. customthe residue was chromatographed on silica gel
  8. custom7.4 g of product were crystallized from appropriate fractions

Sources & evidence

ORD record
ord-0eb8399ccab945c39d4134aaa24a5e2d
Source dataset
uspto-grants-2001_01
Patent number
US06177449B1

Reaction notes

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