Dimethylformamide → HCID 178504028, compound

HRID 1059455Notes

Reaction equation

HRID 1059455 reaction equation
[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.[CH3:20]N(C)C=O.CI.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[N:1]1[C:10]2[NH:9][C:8]3[CH:11]=[C:12]([CH2:15][NH:16][C:17](=[NH:19])[S:18][CH3:20])[CH:13]=[CH:14][C:7]=3[S:6][C:5]=2[N:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18670150HCID 18670150, compound

Product 1

HCID 178504028HCID 178504028, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.0 g of N-(10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)thiourea in acetone (10 ml)/N,N-dimethylformamide (10 ml) was added 1.0 ml of methyl iodide and the resulting mixture was stirred at room temperature for 0.5 hour. Next, the reaction mixture was distributed into an aqueous solution of potassium carbonate and ethyl acetate. The organic layer was extracted and washed with water. After distilling off the solvent under reduced pressure, the crystals thus precipitated were taken up by filtration and washed with ethyl acetate to thereby give 0.900 g of the title compound as yellow crystals.

Workup

  1. extractionThe organic layer was extracted
  2. washwashed with water
  3. distillationAfter distilling off the solvent under reduced pressure
  4. customthe crystals thus precipitated
  5. filtrationwere taken up by filtration
  6. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-4c46e3e2e71b46ba96867fbc1b8e98a2
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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