Acetic Acid → HCID 11086145, compound

HRID 1936562Notes

Reaction equation

HRID 1936562 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[S:13][CH3:14])=[O:5].C(O)(=O)C.CO[CH:21]1[CH2:25][CH2:24][CH:23](OC)O1>O>[F:12][C:10]1[CH:9]=[CH:8][C:7]([S:13][CH3:14])=[C:6]([C:4](=[O:5])[CH2:3][N:2]2[CH:21]=[CH:25][CH:24]=[CH:23]2)[CH:11]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 790982,5-DimethoxytetrahydrofuranHCID 22462180HCID 22462180, compound

Product 1

HCID 11086145HCID 11086145, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 2-amino-1-[5-fluoro-2-(methylthio)phenyl]ethanone hydrochloride (4.54 g, 19.27 mmol) in water (29 ml), heated at 90° C., were added trihydrated sodium acetate (2.62 g, 19.27 mmol), glacial acetic acid (17 ml) and 2,5-dimethoxytetrahydrofuran (2.40 ml, 18.50 mmol). After 20 seconds at 90-100° C. the mixture was cooled and extracted with ethyl acetate. The organic layers were washed with a 20% solution of sodium bicarbonate and brine, dried and evaporated. The residue was chromatographed (50% petroleum ether 40-60° in dichloromethane) to afford 2.07 g of 22c as white crystals mp 133.2-134.0° C. (50% yield). 1H NMR (CDCl3) δ7.39-7.15 (m, 34); 6.66-6.65 (m, 2H); 6.22-6.20 (m, 2H); 5.20 (s, 2H); 2.42 (s, 3H). MS m/z 252 (M++H), 234, 202 (100), 183, 169, 154, 141, 126, 109, 80.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layers were washed with a 20% solution of sodium bicarbonate and brine
  3. customdried
  4. customevaporated
  5. customThe residue was chromatographed (50% petroleum ether 40-60° in dichloromethane)

Sources & evidence

ORD record
ord-1e7ce538761443dfbbc5bcb57818271f
Source dataset
uspto-grants-2002_05
Patent number
US06391870B2

Reaction notes

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