Dimethyl Sulfoxide → HCID 14210538, compound

HRID 2379782Notes

Reaction equation

HRID 2379782 reaction equation
Br[CH:2]1[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[C:11]([O:24][CH3:25])[C:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[CH:13][C:4]=2[CH:3]1O.[NH:27]1[CH2:31][CH2:30][CH2:29][C:28]1=[O:32].[H-].[Na+].CS(C)=[O:37]>>[CH3:9][C:7]1([CH3:8])[O:6][C:5]2[CH:10]=[C:11]([O:24][CH3:25])[C:12]([S:14]([C:17]3[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=3)(=[O:15])=[O:16])=[CH:13][C:4]=2[C@@H:3]([N:27]2[CH2:31][CH2:30][CH2:29][C:28]2=[O:32])[C@@H:2]1[OH:37]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 14210535HCID 14210535, compound

Product 1

HCID 14210538HCID 14210538, compound

Conditions

Temperature
40 °C

Procedure

4,3 g (0.0097 mole) of 3-bromo-3,4-dihydro-2,2-dimethyl-7-methoxy-6-(p-tolylsulfonyl)-2H-benzo[b]pyran-4-ol are dissolved in 28 ml of dimethyl sulfoxide, and 3.5 ml of 2-pyrrolidinone (0.0465 mole) and 0.78 g of sodium hydride (80% suspension in oil) (0.0325 mole) are added, and the mixture is stirred at 40° C. for 3 hours. It is left to stand overnight and then poured onto ice-water and filtered with suction. The precipitate is recrystallized from isopropanol. White crystals of melting point: 263°-65° C.

Workup

  1. waitIt is left
  2. waitto stand overnight
  3. additionpoured onto ice-water
  4. filtrationfiltered with suction
  5. customThe precipitate is recrystallized from isopropanol

Sources & evidence

ORD record
ord-f4ece39ef1a645de935f917d53274ac0
Source dataset
uspto-grants-1994_11
Patent number
US05364878

Reaction notes

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