Butylamine → HCID 178449213, compound

HRID 2379889Notes

Reaction equation

HRID 2379889 reaction equation
I.[C:2]([NH:5][CH2:6][C:7]1[N:12]=[C:11]([C:13]2[N:14]=[C:15]([N:18]=[C:19]([NH2:22])SC)[S:16][CH:17]=2)[CH:10]=[CH:9][CH:8]=1)(=[O:4])[CH3:3].[CH2:23]([NH2:27])[CH2:24][CH2:25][CH3:26]>C(O)C>[C:2]([NH:5][CH2:6][C:7]1[N:12]=[C:11]([C:13]2[N:14]=[C:15]([N:18]=[C:19]([NH2:22])[NH:27][CH2:23][CH2:24][CH2:25][CH3:26])[S:16][CH:17]=2)[CH:10]=[CH:9][CH:8]=1)(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 67820999HCID 67820999, compound

Product 1

HCID 178449213HCID 178449213, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(6-acetylaminomethylpyridin-2-yl)-2-[(amino)(methylthio)methyleneamino]thiazole hydriodide (1.5 g) and n-butylamine (1.6 ml) in ethanol (30 ml) was heated under reflux for 40 hours. The solvent was removed by concentration and residue was added to a mixture of ethyl acetate, tetrahydrofuran and water. The mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate and a 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 chloroform and methanol (19:1, 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 diisopropyl ether to give 4-(6-acetylaminomethylpyridin-2-yl)-2-[(amino) (n-butylamino)methyleneamino]thiazole (0.48 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 40 hours
  3. customThe solvent was removed by concentration and residue
  4. additionwas added to a mixture of ethyl acetate, tetrahydrofuran and water
  5. washa separated organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation of a solvent
  8. customgave a residue, which
  9. customwas purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (19:1, V/V)
  10. additionThe eluted fractions containing the desired product
  11. customwere collected
  12. customevaporated in vacuo
  13. customThe residue was recrystallized from a mixture of methanol, dioxane and diisopropyl ether

Sources & evidence

ORD record
ord-909b42183aa94c29a2d34b6ab5cf2aad
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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