Ammonium Hydroxide → [3-(2-Methoxy-ethoxy)-5-(pyridine-3-yloxy)-pyridine-2-yl]-thiourea

HRID 1966251Notes

Reaction equation

HRID 1966251 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([NH2:19])=[N:8][CH:9]=[C:10]([O:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:11]=1.[C:20](N1C=CN=C1)([N:22]1C=CN=C1)=[S:21].[NH4+].[OH-]>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([NH:19][C:20]([NH2:22])=[S:21])=[N:8][CH:9]=[C:10]([O:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 674865053-(2-Methoxy-ethoxy)-5-(pyridine-3-yloxy)-pyridine-2-ylamine

Product 1

HCID 86644609[3-(2-Methoxy-ethoxy)-5-(pyridine-3-yloxy)-pyridine-2-yl]-thioureaYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Methoxy-ethoxy)-5-(pyridine-3-yloxy)-pyridine-2-ylamine (0.48 mmol) is dissolved in THF (7 ml) and 1,1′-thiocarbonyldiimidazole (4 eq.) is added. The reaction solution is stirred 2 days. 32% NH4OH (20 eq.) is added and stirred 4 hours at room temperature. The solved is removed in vacuo and water (150 ml) is added and extracted with dichloromethane. The combined organic layers are washed with brine and dried over MgSO4. The solvent is removed in vacuo. [3-(2-Methoxy-ethoxy)-5-(pyridine-3-yloxy)-pyridine-2-yl]-thiourea is obtained as yellow solid in a yield of 69%. HPLC (method C): 1.15 min; LC-MS (method A): 0.9 min, 321.15 (MH+).

Workup

  1. stirringstirred 4 hours at room temperature
  2. customThe solved is removed in vacuo and water (150 ml)
  3. additionis added
  4. extractionextracted with dichloromethane
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over MgSO4
  7. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-51cb5a33446f4ade8eddea750ff1bbd2
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

Loading…