Hydrochloric Acid → HCID 57117679, compound

HRID 1439841Notes

Reaction equation

HRID 1439841 reaction equation
C([O:4][C:5]1[CH:22]=[CH:21][C:8]([CH:9]=[C:10]2[C:15](=[O:16])[NH:14][C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[S:11]2)=[CH:7][C:6]=1[C:23]([CH3:26])([CH3:25])[CH3:24])(=O)C.O1CCCC1.[OH-].[Li+].Cl>O.CO>[C:23]([C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][C:5]=1[OH:4])[CH:9]=[C:10]1[C:15](=[O:16])[NH:14][C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[S:11]1)([CH3:26])([CH3:24])[CH3:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 57023106HCID 57023106, compound

Product 1

HCID 57117679HCID 57117679, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(4-acetoxy-3-tert.-butylbenzylidene)-3,4-dihydro-3-oxo-2H-1,4-benzothiazine (Reference compound No. 1-2, 0.31 g) in the mixture of tetrahydrofuran (12 ml) and methanol (3 ml), lithium hydroxide (0.18 g) dissolved in water (8 ml) was added dropwise under ice cooling. After the addition, the mixture was stirred for additional 10 minutes. The reaction mixture was poured into 1N hydrochloric acid and the whole was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo to give 0.25 g (91%) of 2-(3-tert.-butyl-4-hydroxybenzylidene)-3,4-dihydro-3-oxo-2H-1,4-benzothiazine as crystals.

Workup

  1. additionwas added dropwise under ice cooling
  2. additionAfter the addition
  3. extractionthe whole was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6d4d678649641049ca240bad688bdc1
Source dataset
uspto-grants-1996_03
Patent number
US05496817

Reaction notes

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