Water → HCID 66623368, compound

HRID 550753Notes

Reaction equation

HRID 550753 reaction equation
CCN(C1C=CC=CC=1)CC.O[CH:13]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([NH2:20])=[O:19])[CH3:14].S(Cl)([Cl:26])=O.O>C(Cl)Cl>[Cl:26][CH:13]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([NH2:20])=[O:19])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 7061N,N-DiethylanilineHCID 24386Thionyl ChlorideHCID 2812153-(1-Hydroxyethyl)benzamide

Product 1

HCID 66623368HCID 66623368, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethylaniline (390 μL, 2.45 mmol) was added 3-(1-hydroxyethyl)benzamide (400 mg, 2.45 mmol) slurried in DCM (20 mL) and the reaction mixture was cooled with an ice -bath. Thionyl chloride ((255 μL, 2.47 mmol) was added dropwise and the reaction was put in the refrigerator overnight. Water was added, the reaction mixture was extracted twice with DCM, washed with a 10% HCl solution, neutralized with a saturated bicarbonate solution, treated with brine, dried (MgSO4), filtered and evaporated to dryness. The crude product was recrystallized from diethylether/hexane to give 335 mg (75% yield) of the title compound as a white solid.

Workup

  1. customwas put in the refrigerator overnight
  2. extractionthe reaction mixture was extracted twice with DCM
  3. washwashed with a 10% HCl solution
  4. additiontreated with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude product was recrystallized from diethylether/hexane

Sources & evidence

ORD record
ord-077d38408ade483397030dde5c3e8879
Source dataset
uspto-grants-2011_05
Patent number
US07947693B2

Reaction notes

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