Water → [3-(2-Methoxy-ethoxy)-5-phenoxy-pyridine-2-yl]-thiourea

HRID 1966218Notes

Reaction equation

HRID 1966218 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:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=1.[C:20](N1C=CN=C1)([N:22]1C=CN=C1)=[S:21].[NH4+].[OH-].O>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:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 674861883-(2-Methoxyethoxy)-5-phenoxy-pyridine-2-ylamine

Product 1

HCID 86644602[3-(2-Methoxy-ethoxy)-5-phenoxy-pyridine-2-yl]-thioureaYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Methoxy-ethoxy)-5-phenoxy-pyridine-2-ylamine (0.3 mmol) is dissolved in THF (4 ml) and 1,1′-thiocarbonyldiimidazole (4 eq.) is added. The reaction solution is stirred 19 hours. 32% NH4OH (21 eq.) is added and stirred 3 hours at room temperature. Water (50 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-phenoxy-pyridine-2-yl]-thiourea is obtained as brown oil in a yield of 81%; HPLC (method C): 1.85 min; LC-MS (method A): 1.68 min, 320.15 (M+H+).

Workup

  1. stirringstirred 3 hours at room temperature
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over MgSO4
  5. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-7f331400347e4cf7a46b85e3037f8e1d
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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