Diethylamine → HCID 19844244, compound

HRID 34713Notes

Reaction equation

HRID 34713 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[CH2:12]([C:16]1[CH2:17][C:18]2[C:23]([C:24]=1Br)=[CH:22][C:21]1[O:26][CH2:27][O:28][C:20]=1[CH:19]=2)[CH2:13][CH2:14][CH3:15].C(=O)([O-])O.[Na+]>CS(C)=O>[CH2:12]([C:16]1[CH2:17][C:18]2[C:23]([C:24]=1[N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:22][C:21]1[O:26][CH2:27][O:28][C:20]=1[CH:19]=2)[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 19844235HCID 19844235, compound

Product 1

HCID 19844244HCID 19844244, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution containing 300 mg of diethylamine and 430 mg of sodium carbonate in 6 ml of dimethylsulfoxide, 600 mg of 2-n-butyl-3-bromo-5,6-methylenedioxyindene was added at room temperature. The reaction mixture was stirred for 5 hours. After completion of the reaction, the reaction mixture was added with a saturated aqueous solution of sodium hydrogencarbonate and then extracted with ether. The ethereal layer was washed with water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: a 10:1 mixture of n-hexane and ether) to give 380 mg of an oily substance (yield: 65%).

Workup

  1. additionwas added at room temperature
  2. customAfter completion of the reaction
  3. extractionextracted with ether
  4. washThe ethereal layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluent
  8. additiona 10:1 mixture of n-hexane and ether)
  9. customto give 380 mg of an oily substance (yield: 65%)

Sources & evidence

ORD record
ord-ec5128c95a7b4d939402fc3921dc0df6
Source dataset
uspto-grants-1988_08
Patent number
US04762927

Reaction notes

Loading…