Dimethyl Sulfoxide → HCID 67820243, compound

HRID 359042Notes

Reaction equation

HRID 359042 reaction equation
[H-].[Na+].Br[CH:4]1[C:9]([CH3:11])([CH3:10])[O:8][C:7]2[CH:12]=[CH:13][C:14]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:15][C:6]=2[CH:5]1O.[NH:27]1[CH2:31][CH2:30][CH2:29][C:28]1=[O:32].CS(C)=[O:35]>>[CH3:10][C:9]1([CH3:11])[O:8][C:7]2[CH:12]=[CH:13][C:14]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:15][C:6]=2[C@@H:5]([N:27]2[CH2:31][CH2:30][CH2:29][C:28]2=[O:32])[C@@H:4]1[OH:35]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 120252-PyrrolidoneHCID 24758Sodium hydride2×HCID 14210536HCID 14210536, compound

Product 1

HCID 67820243HCID 67820243, compound

Procedure

0.75 g (0.025 mol) of 80 % NaH is introduced into 8.2 g (0.02 mol) of 3-bromo-3,4-dihydro-2,2-dimethyl-6-(4'-methyl-phenylsulfonyl)-2H-benzo[b]pyran -4-ol in 30 ml of dimethyl of dimethyl sulfoxide. After stirring for one hour at 20°, a further 0.75 g (0.025 mol) of 80 % NaH and 1.9 ml (0.025 mol) of 2-pyrrolidone are added and the mixture is stirred for 45 minutes at 40° and for 6 hours at 20°. After the mixture has been introduced into ice water, the precipitate is filtered off with suction, dried and recrystallized several times from methanol. Crystals of melting point: 242-243°.

Workup

  1. stirringthe mixture is stirred for 45 minutes at 40° and for 6 hours at 20°
  2. filtrationthe precipitate is filtered off with suction
  3. customdried
  4. customrecrystallized several times from methanol

Sources & evidence

ORD record
ord-75f28ff4edcc4a5e81ff5b036fff11c2
Source dataset
uspto-grants-1991_03
Patent number
US04999371

Reaction notes

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