Sodium Bicarbonate → HCID 136046842, compound

HRID 1463474Notes

Reaction equation

HRID 1463474 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21]CSC)[CH:6]=[CH:7][C:8]1[S:9][C:10]2[NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]=2[N:17]=1.C(=O)([O-])O.[Na+]>CN(C)C=O.C(#N)C.O>[OH:21][C:20]1[CH:19]=[CH:18][C:5]([CH:6]=[CH:7][C:8]2[S:9][C:10]3[NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]=3[N:17]=2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 54568716HCID 54568716, compound

Product 1

HCID 136046842HCID 136046842, compoundYield 20.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

2-(3-Methoxy-4-methylthiomethoxystyryl)-5,6,7,8-tetrahydro-4H-thiazolo[5,4-b]azepine (1.88 g) obtained in Example 87, was dissolved in a mixture of dimethylformamide, acetonitrile and water, following by addition of mercuric chloride (2.11 g). The mixture was refluxed for 15 hrs. After completing the reaction, an aqueous sodium hydrogen carbonate was added to the mixture. The mixture was extracted with a mixture of chloroform and methanol, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was subjected to a column chromatography on silica gel eluting a mixture of chloroform and methanol (98:2, v/v) to give the title compound (yield 318 mg).

Workup

  1. temperatureThe mixture was refluxed for 15 hrs
  2. customthe reaction
  3. extractionThe mixture was extracted with a mixture of chloroform and methanol
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. additiona mixture of chloroform and methanol (98:2, v/v)

Sources & evidence

ORD record
ord-24ec2d553a7c4a20b55afbf507e8bcbb
Source dataset
uspto-grants-1994_04
Patent number
US05300639

Reaction notes

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