Water → HCID 66623368, compound

HRID 60524Notes

Reaction equation

HRID 60524 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. temperaturethe reaction mixture was cooled with an ice-bath
  2. customwas put in the refrigerator overnight
  3. extractionthe reaction mixture was extracted twice with DCM
  4. washwashed with a 10% HCl solution
  5. additiontreated with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe crude product was recrystallized from diethylether/hexane

Sources & evidence

ORD record
ord-8b1e0e37f0494fc1bfa468993a4babe8
Source dataset
uspto-grants-2016_09
Patent number
US09440992B2

Reaction notes

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