Iodoethane → N-[6-Benzyloxy-2,2-dimethylchroman-4-yl]-N-ethylmethanesulfonamide

HRID 567058Notes

Reaction equation

HRID 567058 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+].[CH2:28](I)[CH3:29]>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]([CH2:28][CH3:29])[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 6340IodoethaneHCID 24758Sodium hydrideHCID 212645206-Benzyloxy-4-(methylsulfonyl)amino-2,2-dimethylchroman

Product 1

HCID 21264511N-[6-Benzyloxy-2,2-dimethylchroman-4-yl]-N-ethylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

7.2 g (20 mmol) of 6-benzyloxy-4-(methylsulfonyl)amino-2,2-dimethylchroman were introduced in portions at 10° C. into a suspension of 0.82 g (27 mmol) of sodium hydride (80 per cent dispersion) in 60 ml of DMA. After stirring at RT for 2 h, 2.2 ml (26.5 mmol) of ethyl iodide were added dropwise, the temperature rising to 32° C. The mixture was then heated to 35-40° C. for 2 h, concentrated in vac., treated with water, the resinous product was taken up EA, the solution was dried and concentrated and the residue was chromatographed using n-heptane/EA (2:1) on silica gel. 6 g of product were crystallized from appropriate fractions using petroleum ether/diisopropyl ether (1:1), m.p. 104-106° C.

Workup

  1. customrising to 32° C
  2. temperatureThe mixture was then heated to 35-40° C. for 2 h
  3. concentrationconcentrated in vac
  4. addition, treated with water
  5. customthe solution was dried
  6. concentrationconcentrated
  7. customthe residue was chromatographed
  8. custom6 g of product were crystallized from appropriate fractions

Sources & evidence

ORD record
ord-60ee6c077eff4c2b9e9ab0fcf460a589
Source dataset
uspto-grants-2001_01
Patent number
US06177449B1

Reaction notes

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