Triethylamine → HCID 18753581, compound

HRID 1838426Notes

Reaction equation

HRID 1838426 reaction equation
C(N(CC)CC)C.[NH2:8][CH:9]([CH2:12][OH:13])[CH2:10][OH:11].[O:14]([C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCOCC1.O>[O:14]([C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:8][CH:9]([CH2:12][OH:13])[CH2:10][OH:11])(=[O:29])=[O:28])=[CH:23][CH:22]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 68294SerinolHCID 27947564-Phenoxybenzene-1-sulfonyl chloride

Product 1

HCID 18753581HCID 18753581, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

After triethylamine (10.12 g, 100 mmol) was added dropwise to a solution of serinol (3.64 g, 40 mmol) in a mixture of dioxane (100 ml) and water (200 ml), the mixture was stirred at room temperature for 30 minutes. To the reaction mixture, a solution of 4-phenoxybenzenesulfonyl chloride (10.75 g, 40 mmol) in dioxane (100 ml) was added dropwise and this was stirred for 3 hours. Most of the solvent was evaporated under reduced pressure and the residue was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the desired compound (10.62 g, yield 82%) as a white powder.

Workup

  1. stirringthis was stirred for 3 hours
  2. customMost of the solvent was evaporated under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8d5170afc94143539633d78b0740cded
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

Loading…