Water → HCID 24899058, compound

HRID 2382591Notes

Reaction equation

HRID 2382591 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:16][C:15]2[CH:17]=[C:18]([CH:21]=[C:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])[CH:19]=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]1.O>COCCOC>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:16][C:15]2[CH:17]=[C:18]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])[CH:19]=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 962WaterHCID 74348953HCID 74348953, compound2×

Product 1

HCID 24899058HCID 24899058, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
8.5 °C

Procedure

5-(4-Benzooxazol-2-yl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-7-ylmethylene)-thiazolidine-2,4-dione [compound of Example 6] (0.118 g, 0.3 mmol) was taken in 1,2-dimethoxyethane (40 mL) under nitrogen. The mixture was cooled to 7-10° C. by using dry ice-acetone bath, freshly prepared Al-amalgam strips and water (0.54 mL, 30 mmol) were added and the reaction mixture was stirred for 4 hours. The reaction mixture was then filtered through a celite bed and washed with 1,2-dimethoxyethane. The organic layer was concentrated under high vacuum and purified using silica gel column in 50% ethyl acetate in petroleum ether. The product obtained after concentration was washed with 2% ethyl acetate in petroleum ether, to give 5-(4-benzooxazol-2-yl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-7-ylmethyl)-thiazolidine-2,4-dione.

Workup

  1. filtrationThe reaction mixture was then filtered through a celite bed
  2. washwashed with 1,2-dimethoxyethane
  3. concentrationThe organic layer was concentrated under high vacuum
  4. custompurified
  5. customThe product obtained
  6. concentrationafter concentration
  7. washwas washed with 2% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-406e2d74a52a4945b99264ef7947e191
Source dataset
uspto-grants-2012_09
Patent number
US08263587B2

Reaction notes

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