Potassium Carbonate → HCID 178504863, compound

HRID 1699404Notes

Reaction equation

HRID 1699404 reaction equation
[CH3:1]S[CH2:3][C:4]1[C:14]2[O:13][CH2:12][CH2:11][C:10]([C:15]([NH:17][C:18]([NH2:20])=[NH:19])=[O:16])=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.Cl[C:22]1C=CC=C(C(OO)=O)C=1.[S:32]([O-:36])([O-:35])(=[O:34])=S.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.CO>[CH3:1][S:32]([OH:36])(=[O:35])=[O:34].[CH3:22][S:32]([CH2:3][C:4]1[C:14]2[O:13][CH2:12][CH2:11][C:10]([C:15]([NH:17][C:18]([NH2:20])=[NH:19])=[O:16])=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:36])=[O:34]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 178503654HCID 178503654, compound

Product 1

HCID 178504863HCID 178504863, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

The mixture of (2,3-dihydro-9-methylthiomethyl-1-benzoxepin-4-carbonyl)guanidine (0.4 g) and m-chloroperbenzoic acid (0.52 g) in chloroform (20 ml) and methanol (4 ml) was stirred at ambient temperature for 2 hours. The reaction mixture was added to 10% aqueous sodium thiosulfate, adjusted to pH 9 with 20% aqueous potassium carbonate and extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract layer was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was dissolved in methanol (5 ml), and methanesulfonic acid (0.11 ml) was added with stirring. To the mixture was added diisopropyl ether (5 ml) and isolated crystalline was collected by filtration. The crystalline was recrystallized from a mixture of methanol and diisopropyl ether to give (2,3-dihydro-9-methanesulfonylmethyl-1-benzoxepin-4-carbonyl)guanidine methanesulfonate (0.16 g).

Workup

  1. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran
  2. washThe extract layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. dissolutionThe residue was dissolved in methanol (5 ml)
  6. additionmethanesulfonic acid (0.11 ml) was added
  7. stirringwith stirring
  8. additionTo the mixture was added diisopropyl ether (5 ml)
  9. customisolated crystalline
  10. filtrationwas collected by filtration
  11. customThe crystalline was recrystallized from a mixture of methanol and diisopropyl ether

Sources & evidence

ORD record
ord-9d293b406f574e219d46437d1be48f51
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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