Methyl iodide → HCID 21264532, compound

HRID 567065Notes

Reaction equation

HRID 567065 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]([CH2:25][CH3:26])(=[O:24])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:29]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]([CH3:29])[S:22]([CH2:25][CH3:26])(=[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 21264526HCID 21264526, compound

Product 1

HCID 21264532HCID 21264532, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Analogously to Example 1f, 8.6 g (23 mmol) of 6-benzyloxy-4-(ethylsulfonyl)amino-2,2-dimethylchroman were introduced in portions into a suspension of 1 g (25 mmol) of sodium hydride (60% dispersion) in 75 ml of DMA at 10° C. After stirring at RT for 2 h, 1.6 ml (25 mmol) of methyl iodide were added dropwise, the temperature rising to 40° C. The mixture was then heated to 35-45° C. for 2 h, and concentrated in vacuo, 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 using n-heptane/EA (1:1) on silica gel. 7.4 g of product were crystallized from appropriate fractions using petroleum ether/diisopropyl ether, m.p. 91-93° C.

Workup

  1. customrising to 40° C
  2. temperatureThe mixture was then heated to 35-45° C. for 2 h
  3. concentrationconcentrated in vacuo
  4. additionthe residue was treated with water
  5. customthe solution was dried
  6. concentrationconcentrated
  7. customthe residue was chromatographed
  8. custom7.4 g of product were crystallized from appropriate fractions

Sources & evidence

ORD record
ord-86b0635b9b1b423c95c9f16cb119b5b8
Source dataset
uspto-grants-2001_01
Patent number
US06177449B1

Reaction notes

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