Water → HCID 66623368, compound

HRID 415360Notes

Reaction equation

HRID 415360 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%) 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-5299feeb6814475889fedd5a6f8fe537
Source dataset
uspto-grants-2012_01
Patent number
US08088780B2

Reaction notes

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