Water → HCID 10341350, compound

HRID 1033068Notes

Reaction equation

HRID 1033068 reaction equation
[NH2:1][C:2](=[N:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[O:11][C:12]([CH2:15][NH:16][C:17](=[O:26])[CH2:18][S:19][CH2:20][C:21]3[O:22][CH:23]=[CH:24][CH:25]=3)=[CH:13][CH:14]=2)[N:9]=1)[NH2:3].ClC1C=CC=C(C(OO)=[O:35])C=1.O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2](=[N:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[O:11][C:12]([CH2:15][NH:16][C:17](=[O:26])[CH2:18][S:19]([CH2:20][C:21]3[O:22][CH:23]=[CH:24][CH:25]=3)=[O:35])=[CH:13][CH:14]=2)[N:9]=1)[NH2:3]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 10318301HCID 10318301, compound

Product 1

HCID 10341350HCID 10341350, compoundYield 96.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(diaminomethyleneamino)-4-[5-{(furan-2-yl)methylthio}acetamidomethylfuran-2-yl]thiazole (1.5 g) and 3-chloroperbenzoic acid (0.9 g) in a mixture of tetrahydrofuran (30 ml) and N,N-dimethylformamide (10 ml) was stirred for 1.5 hours at ambient temperature. To the reaction mixture was added a solution of water and ethyl acetate and the mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. Evaporation of a solvent gave a residue, which was purified by column chromatography on silica gel eluting with a mixture of ethyl acetate and methanol (9:1, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo. The residue was recrystallized from a mixture of methanol, dioxane and isopropyl ether to give 2-(diaminomethyleneamino)-4-[5-{(furan-2-yl)methylsulfinyl}acetamidomethylfuran-2-yl]thiazole (1.5 g).

Workup

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of a solvent
  4. customgave a residue, which
  5. customwas purified by column chromatography on silica gel eluting with a mixture of ethyl acetate and methanol (9:1, V/V)
  6. additionThe eluted fractions containing the desired product
  7. customwere collected
  8. customevaporated in vacuo
  9. customThe residue was recrystallized from a mixture of methanol, dioxane and isopropyl ether

Sources & evidence

ORD record
ord-bc4c4c31a42a47bcba7e2c9755554dbe
Source dataset
uspto-grants-1994_05
Patent number
US05308857

Reaction notes

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