Diethyl Ether → HCID 178515339, compound

HRID 40687Notes

Reaction equation

HRID 40687 reaction equation
C(O[CH:4](OCC)[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15])=[O:6])C.[OH-].[NH4+].CCOCC>S(=O)(=O)(O)O>[F:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[CH:8]=[N:7][C:5]([OH:6])=[CH:4]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14923Ammonium HydroxideHCID 596364612,2-Diethoxy-N-(2-fluorobenzyl)acetamide

Product 1

HCID 178515339HCID 178515339, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2,2-Diethoxy-N-(2-fluorobenzyl)acetamide (4.1 g, 16.0 mmol) was stirred in concentrated sulfuric acid (10 mL) for 16 hours. The reaction mixture was poured onto ice and neutralized by the addition of ammonium hydroxide forming a precipitate which was removed by filtration. The filtrate was extracted with ethyl acetate three times, and the combined organic phases were rinsed with brine then dried (Na2SO4) and concentrated to dryness affording an oily solid. Trituration with ether afforded the title compound (1.56 g, 9.6 mmol, 60% over 2 steps). LC-MS (3) Rt=1.00 min; m/z (ESI+) 164 (M+H).

Workup

  1. additionThe reaction mixture was poured onto ice
  2. customwas removed by filtration
  3. extractionThe filtrate was extracted with ethyl acetate three times
  4. washthe combined organic phases were rinsed with brine
  5. dry with materialthen dried (Na2SO4)
  6. concentrationconcentrated to dryness
  7. customaffording an oily solid

Sources & evidence

ORD record
ord-34bc098bce344f4e98ab647eeceb8321
Source dataset
uspto-grants-2013_09
Patent number
US08530468B2

Reaction notes

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