Acetic Acid → HCID 23001316, compound

HRID 844267Notes

Reaction equation

HRID 844267 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:13]3[CH:14]=[CH:15][N:16]=[C:12]3[CH2:11][CH2:10]2)=[CH:5][C:4]=1[F:17])#[N:2].[C:18]([O-])(=[O:20])C.[Na+].C(O)(=O)C.C=O>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:13]3[C:14]([CH2:18][OH:20])=[CH:15][N:16]=[C:12]3[CH2:11][CH2:10]2)=[CH:5][C:4]=1[F:17])#[N:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 517045Sodium AcetateHCID 23001282HCID 23001282, compound

Product 1

HCID 23001316HCID 23001316, compound

Procedure

A solution of product from Step H (3.79 g, 16.7 mmol), sodium acetate (2.44 g, 29.7 mmol), acetic acid (1.82 mL, 31.9 mmol), and formaldehyde (37% in water, 15.1 mL) was heated to reflux for 96 hours. The reaction was slowly neutralized by the addition of sat. aq. NAHCO3. The aqueous layer was extracted with methylene chloride (5×50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by column chromatography (1→10% MeOH/CHCl3) to provide the title compound as a white solid.

Workup

  1. temperatureto reflux for 96 hours
  2. additionThe reaction was slowly neutralized by the addition of sat. aq. NAHCO3
  3. extractionThe aqueous layer was extracted with methylene chloride (5×50 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (1→10% MeOH/CHCl3)

Sources & evidence

ORD record
ord-8af20aff8cf54cc897b96110f6a3e32e
Source dataset
uspto-grants-2002_04
Patent number
US06380228B1

Reaction notes

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