Methanol, 1,1-diethoxy-, 1-acetate → 8-[Ethoxymethylidene]-6H-[1,3]thiazolo[5,4-e]indol-7-one

HRID 2297861Notes

Reaction equation

HRID 2297861 reaction equation
[S:1]1[C:5]2=[C:6]3[C:10](=[CH:11][CH:12]=[C:4]2[N:3]=[CH:2]1)[NH:9][C:8](=[O:13])[CH2:7]3.[C:14]([O:17][CH:18](OCC)OCC)(=O)[CH3:15]>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>[CH2:14]([O:17][CH:18]=[C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]3[N:3]=[CH:2][S:1][C:5]3=2)[NH:9][C:8]1=[O:13])[CH3:15]

Participants

4

Reactant 2

HCID 84166Methanol, 1,1-diethoxy-, 1-acetateHCID 111168276H-thiazolo[5,4-e]indol-7(8H)-one

Product 1

HCID 539908078-[Ethoxymethylidene]-6H-[1,3]thiazolo[5,4-e]indol-7-one

Reagents, catalysts & solvents 1

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Procedure

To a 250-mi round bottom flask was added a stir bar, 6,8-dihydro-7H-[1,3]thiazolo[5,4-e]indol-7-one (4.0 g, 0.021 mol), 40 mL of glacial acetic and diethoxymethyl acetate (17.0 g, 0.105 moles). The flask was fitted with a reflux condensor and charged with nitrogen. The reaction was heated to reflux for 8 h. The flask was cooled, the stir bar was removed and the reaction was concentrated to a wet solid. The solid was triturated with a solution of ether and ethanol. The mixture was filtered, and the solid was washed with an ethanol-ether solution and was dried under vacuum to yield the title compound: 1H NMR (DMSO-d6):δ 10.5 (s, 1H), 9.1 (s, 1H), 7.8 (d, 1H), 7.7 (s, 1H), 7.0 (d, 1H), 4.5 (q, 2H), 1.4 (t, 3H); APCI-MS m/z 245 (M-H)−.

Workup

  1. additionTo a 250-mi round bottom flask was added a stir bar
  2. customThe flask was fitted with a reflux condensor
  3. additioncharged with nitrogen
  4. temperatureThe reaction was heated
  5. temperatureto reflux for 8 h
  6. temperatureThe flask was cooled
  7. customthe stir bar was removed
  8. concentrationthe reaction was concentrated to a wet solid
  9. customThe solid was triturated with a solution of ether and ethanol
  10. filtrationThe mixture was filtered
  11. washthe solid was washed with an ethanol-ether solution
  12. customwas dried under vacuum

Sources & evidence

ORD record
ord-03f8cb262d7c470abf69011b87f91bab
Source dataset
uspto-grants-2002_12
Patent number
US06492398B1

Reaction notes

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