Water → 3-amino-6-(1-phenylcyclopropyl)pyridine-2(1H)-thione

HRID 1177414Notes

Reaction equation

HRID 1177414 reaction equation
CC1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([C:11]1([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:13][CH2:12]1)[N:5]=2.[OH-].[Na+].O>CCO>[NH2:10][C:9]1[C:4](=[S:3])[NH:5][C:6]([C:11]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:13][CH2:12]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 671116252-Methyl-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine

Product 1

HCID 591748363-amino-6-(1-phenylcyclopropyl)pyridine-2(1H)-thione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A slurry of 2-methyl-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (17.0 g, 63.8 mmol) in 128 mL EtOH was added sodium hydroxide 10 M in water (128 mL, 1276 mmol). Argon was bubbled through the resulting slurry for 5 min, then the reaction flask was fitted with a water-cooled reflux condenser, flushed with argon, and the reaction mixture was heated to vigorous reflux under argon. After 6 h, the reaction mixture was cooled and the EtOH was removed in vacuo. The resulting slurry was poured onto ice and neutralized with 260 mL 5N aq. HCl to pH 4. A light yellow precipitate resulted. The solid was collected by filtration through a glass frit, rinsing with 2×200 mL water, and the solid was dried under a bag of nitrogen overnight. Further drying in vacuo for several hours gave 3-amino-6-(1-phenylcyclopropyl)pyridine-2(1H)-thione as a light yellow solid. MS (ESI) m/z: calculated: 242.1; Observed: 243.1 (M++1).

Workup

  1. customArgon was bubbled through the resulting slurry for 5 min
  2. customthe reaction flask was fitted with a water-
  3. temperaturecooled
  4. temperaturereflux condenser
  5. customflushed with argon
  6. temperaturethe reaction mixture was heated
  7. temperatureto vigorous reflux under argon
  8. temperaturethe reaction mixture was cooled
  9. customthe EtOH was removed in vacuo
  10. additionThe resulting slurry was poured onto ice and neutralized with 260 mL 5N aq. HCl to pH 4
  11. customA light yellow precipitate resulted
  12. filtrationThe solid was collected by filtration through a glass frit
  13. washrinsing with 2×200 mL water
  14. customthe solid was dried under a bag of nitrogen overnight
  15. customFurther drying in vacuo for several hours

Sources & evidence

ORD record
ord-ffee17c942854adcab7c605c856bd150
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

Loading…