Sodium Bicarbonate → HCID 10450614, compound

HRID 1374517Notes

Reaction equation

HRID 1374517 reaction equation
[CH3:1][N:2]([CH3:33])[CH2:3][CH2:4][O:5][CH2:6][C:7]1[N:16](COCC[Si](C)(C)C)[C:15]2[C:14]3[CH:25]=[CH:26][CH:27]=[CH:28][C:13]=3[S:12][C:11]3[CH:29]=[CH:30][CH:31]=[CH:32][C:10]=3[C:9]=2[N:8]=1.C(=O)([O-])O.[Na+]>CO.Cl.O>[CH3:1][N:2]([CH3:33])[CH2:3][CH2:4][O:5][CH2:6][C:7]1[NH:16][C:15]2[C:14]3[CH:25]=[CH:26][CH:27]=[CH:28][C:13]=3[S:12][C:11]3[CH:29]=[CH:30][CH:31]=[CH:32][C:10]=3[C:9]=2[N:8]=1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 10412953HCID 10412953, compound

Product 1

HCID 10450614HCID 10450614, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of dimethyl-{2-[1-(2-trimethylsilyl-ethoxymethyl)-1H-8-thia-1,3-diaza-dibenzo[e,h]azulene-2-ylmethoxy]-ethyl}-amine (0.32 mmole) in methanol (7.0 ml), 0.5 M hydrochloric acid in methanol (3.2 ml) was slowly added. The reaction mixture was heated under reflux for 3 hours, then it was cooled to room temperature, neutralized with a saturated aqueous solution of sodium hydrogencarbonate, diluted with water and extracted with dichloromethane. The organic extract was washed with an aqueous sodium chloride solution, dried over anhydrous Na2SO4 and evaporated under reduced pressure. After purification by chromatography on a silica gel column, dimethyl-[2-(1H-8-thia-1,3-diaza-dibenzo[e,h]azulene-2-ylmethoxy)-ethyl]-amine in the form of an oily product was isolated;

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with dichloromethane
  4. extractionThe organic extract
  5. washwas washed with an aqueous sodium chloride solution
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated under reduced pressure
  8. customAfter purification by chromatography on a silica gel column, dimethyl-[2-(1H-8-thia-1,3-diaza-dibenzo[e,h]azulene-2-ylmethoxy)-ethyl]-amine in the form of an oily product
  9. customwas isolated

Sources & evidence

ORD record
ord-5e45572115874612a0a882a740e34b29
Source dataset
uspto-grants-2007_01
Patent number
US07166583B2

Reaction notes

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