Methanol → HCID 18670150, compound

HRID 1059438Notes

Reaction equation

HRID 1059438 reaction equation
[N:1]1[C:10]2[NH:9][C:8]3[CH:11]=[C:12]([CH2:15][NH:16][C:17]([NH:19]C(=O)C4C=CC=CC=4)=[S:18])[CH:13]=[CH:14][C:7]=3[S:6][C:5]=2[N:4]=[CH:3][CH:2]=1.[OH-].[K+].CO.O1CCCC1>C(OCC)(=O)C.O>[N:1]1[C:10]2[NH:9][C:8]3[CH:11]=[C:12]([CH2:15][NH:16][C:17]([NH2:19])=[S:18])[CH:13]=[CH:14][C:7]=3[S:6][C:5]=2[N:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 18670290HCID 18670290, compound

Product 1

HCID 18670150HCID 18670150, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

250 mg of N-(10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)-N′-benzoylthiourea was added to a mixture of a 20% aqueous solution of potassium hydroxide (5 ml) with methanol (5 ml). After further adding a small portion of tetrahydrofuran, the resulting mixture was heated to 50° C. for 5 minutes. Then the reaction mixture was brought back to room temperature and distributed into water and ethyl acetate. The organic layer was extracted, washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the crystals thus precipitated were suspended in ethyl acetate and filtered. Thus, 140 mg of the title compound was obtained as yellow crystals.

Workup

  1. customwas brought back to room temperature
  2. extractionThe organic layer was extracted
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe crystals thus precipitated
  7. filtrationfiltered

Sources & evidence

ORD record
ord-15b6581a9fd242419c522cdd03a64058
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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