Ethyl Acetate → HCID 86684652, compound

HRID 921587Notes

Reaction equation

HRID 921587 reaction equation
[N+:1]([C:4]1[CH:30]=[CH:29][C:7]([CH2:8][C:9]2([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=3)[CH2:15][O:14][C:13]3=[CH:16][S:17][CH:18]=[C:12]3[O:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O.O.O.[Sn](Cl)Cl.C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[NH2:1][C:4]1[CH:30]=[CH:29][C:7]([CH2:8][C:9]2([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=3)[CH2:15][O:14][C:13]3=[CH:16][S:17][CH:18]=[C:12]3[O:11][CH2:10]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 61436Stannous chloride dihydrateHCID 86684653HCID 86684653, compound

Product 1

HCID 86684652HCID 86684652, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(See Scheme, FIG. 7). To a 200 mL round bottom flask was added 0.307 g (0.722 mmol) of 3,3-Bis(4-nitrobenzyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]-dioxepine, 2.1 g (9.3 mmol) of tin(II) chloride dihydrate and 50 mL of ethyl acetate. The solution was heated to reflux for overnight. After heating, the mixture was allowed to cool to room temperature. After cooling, 20 mL of a 0.25 M solution of sodium carbonate and 100 mL of dichloromethane were added. This mixture was vigorously stirred for 30 minutes. The mixture was then filtered through a celite pad and poured into a 500 mL separatory funnel. The organic layer was removed and washed twice with 50 mL of water and once with 50 mL of brine. The solution was dried with MgSO4 and the solvent was removed in vacuo to give the product, 3,3-bis(4-aminobenzyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]-dioxepine, in quantitative yield. IR, 1HNMR, 13CNMR in addition to TLC were used to confirm identity of the product.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for overnight
  3. temperatureAfter heating
  4. temperatureAfter cooling
  5. filtrationThe mixture was then filtered through a celite pad
  6. additionpoured into a 500 mL separatory funnel
  7. customThe organic layer was removed
  8. washwashed twice with 50 mL of water and once with 50 mL of brine
  9. dry with materialThe solution was dried with MgSO4
  10. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f6cedb922b2b436bae35f498418403b8
Source dataset
uspto-grants-2016_03
Patent number
US09274395B2

Reaction notes

Loading…