Dimethyl Sulfoxide → HCID 14210536, compound

HRID 2379785Notes

Reaction equation

HRID 2379785 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1([CH3:30])[CH:19]=C[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:16]=2)[O:11]1.CS(C)=O.C(O)(C)C.[C:39](=[O:41])=O>O>[Br:1][CH:19]1[C:10]([CH3:30])([CH3:9])[O:11][C:12]2[CH:17]=[CH:16][C:15]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])=[CH:14][C:13]=2[CH:39]1[OH:41]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 67184N-bromobutanimideHCID 14210534HCID 14210534, compoundHCID 86586944Isopropanol carbon dioxide

Product 1

HCID 14210536HCID 14210536, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

14.2 g (0.08 mole) of freshly recrystallized N-bromosuccinimide are introduced into 12.6 g (0.04 mole) of 2,2-dimethyl-6-(4-methylphenylsulfonyl)chromene in a solution composed of 70 ml of dimethyl sulfoxide and 1.4 ml of water while cooling (isopropanol/dry ice) at about 15° C. The temperature rises transiently to 27°. It is cooled to 20° C. and, after stirring for one hour, introduced into ice/ethyl acetate. The ethyl acetate phase is washed several times with water and dried over Na2SO4. The bromohydrin derivative crystallizes on concentration. Crystals of melting point: 141°-142° C.

Workup

  1. customrises transiently to 27°
  2. washThe ethyl acetate phase is washed several times with water
  3. dry with materialdried over Na2SO4
  4. customThe bromohydrin derivative crystallizes on concentration

Sources & evidence

ORD record
ord-947a3c659cf6472cba171284f14152cc
Source dataset
uspto-grants-1994_11
Patent number
US05364878

Reaction notes

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