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

HRID 2415069Notes

Reaction equation

HRID 2415069 reaction equation
[S:1]1[C:12]2[C:4](=[CH:5][CH:6]=[C:7]3[C:11]=2[CH2:10][C:9](=[O:13])[NH:8]3)[N:3]=[CH:2]1.[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:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]3[C:12]=2[S:1][CH:2]=[N:3]3)[NH:8][C:9]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-ml round bottom flask was added a stir bar, 6,8-dihydro-1-thia-3,6-diaza-as-indacen-7-one (Procedure B, 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, the solid was washed with an ethanol-ether solution, and the solid was dried under vacuum to yield 8-ethoxymethylene-6,8-dihydro-1-thia-3,6-diaza-as-indacen-7-one: 1H NMR (DMSO-d6): δ10.5 (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-ml 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. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-c4a8d72819d84ef8a43b9c362bdb0007
Source dataset
uspto-grants-2004_11
Patent number
US06818632B2

Reaction notes

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