Acetic Acid → HCID 18439772, compound

HRID 457569Notes

Reaction equation

HRID 457569 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)=[O:4].C1SC(=O)[NH:16][C:14]1=[O:15].C([O-])([O-])=O.[K+].[K+].O.[OH-].[Li+].C(O)(=O)C>CN(C=O)C.O.C1COCC1>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:3]2[O:4][C:14](=[O:15])[NH:16][CH:2]=2)[CH:10]=[CH:9][CH:8]=1

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 11430Potassium CarbonateHCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 18439772HCID 18439772, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromo-3′-methoxyacetophenone (40.0 g, 0.18 mol) and thiazolidinedione (24.5 g, 0.21 mol) in dry DMF (175 mL) was treated with K2CO3 (36.2 g, 0.26 mol) and stirred at RT for 1.5 h. The reaction mixture was slowly poured into ice water (1.7 L). The resulting pink solid, was collected by filtration and washed with water (200 mL). (Excess water was removed by suction) The filter cake was stirred at RT for 30 min in an aqueous solution (350 mL),of lithium hydroxide-hydrate (29.3 g, 0.7 mol) and THF (350 mL). After ice water (700 mL) was added, the suspension was slowly poured into a stirred solution of acetic acid (40 mL, 0.70 mol) in water (1.7 L). The resulting tan solid was collected by filtration, washed with water (500 mL), and dried under vacuum to afford the title compound (23.8 g, 72%). 1H NMR (300 MHz, d6-DMSO): δ 3.80 (s, 3H), 6.86 (dd, 1H, J1=8.1, J2=2.4 Hz), 7.05 (bs, 1H), 7.09 (d, 1H, J=7.8), 7.33 (t, 1H, J=8.1), 7.54 (s, 1H).

Workup

  1. filtrationThe resulting pink solid, was collected by filtration
  2. washwashed with water (200 mL)
  3. custom(Excess water was removed by suction) The filter cake
  4. filtrationThe resulting tan solid was collected by filtration
  5. washwashed with water (500 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-55ee387fc4134397b6c49ccbcdc0097a
Source dataset
uspto-grants-2007_03
Patent number
US07189712B2

Reaction notes

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