Ethanol → HCID 24899056, compound

HRID 2382584Notes

Reaction equation

HRID 2382584 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:13][C:12]2[CH:14]=[C:15]([CH:18]=[C:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])[CH:16]=[CH:17][C:11]=2[O:10][CH2:9][CH2:8]1.[Al].C(OCC)C.C(O)C>COCCOC.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:13][C:12]2[CH:14]=[C:15]([CH2:18][CH:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])[CH:16]=[CH:17][C:11]=2[O:10][CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 702Ethanol2×HCID 3283Diethyl Ether2×HCID 5359268AluminumHCID 74348952HCID 74348952, compound

Product 1

HCID 24899056HCID 24899056, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
-2.5 °C

Procedure

5-(4-Pyridin-2-yl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-7-ylmethylene)-thiazolidine -2,4-dione [compound of Example 3] (0.54 g, 1.5 mmol) was taken in 1,2-dimethoxyethane (45 mL) and heated to dissolve. The reaction mixture was then cooled to −5 to 0° C. and to this solution kept under nitrogen, were added pieces of aluminum foil (10×10×0.02 mm, 0.306 g, 11.3 mmol) which had been freshly dipped for 10 seconds sequentially in each of diethyl ether, ethanol, 2% aqueous mercuric chloride solution, ethanol and again diethyl ether. To the reaction mixture, water was added (0.45 mL), and stirred for 3.5 hours at −5 to 0° C. under N2 atmosphere. To this solution, celite (2.4 g) was added, stirred at room temperature for 5 min, filtered through a celite bed and washed with DMF (3×60 mL). The filtrate was concentrated to give crude material (0.820 g) which was purified by silica chromatography using 1% CH2Cl2 in MeOH, to give 5-(4-pyridin-2-yl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-7-yl-methyl)-thiazolidine-2,4-dione.

Workup

  1. temperatureheated to dissolve
  2. additionTo this solution, celite (2.4 g) was added
  3. stirringstirred at room temperature for 5 min
  4. filtrationfiltered through a celite bed
  5. washwashed with DMF (3×60 mL)
  6. concentrationThe filtrate was concentrated
  7. customto give crude material (0.820 g) which
  8. customwas purified by silica chromatography

Sources & evidence

ORD record
ord-3f96cf8af18c46fb9e54c2507e2777d6
Source dataset
uspto-grants-2012_09
Patent number
US08263587B2

Reaction notes

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