Water → [3-(2-Methoxy-1-methyl-ethoxy)-5-phenoxy-pyridin-2-yl]thiourea

HRID 1966240Notes

Reaction equation

HRID 1966240 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([CH3:20])[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:21](N1C=CN=C1)([N:23]1C=CN=C1)=[S:22].[NH4+].[OH-].O>C1COCC1>[CH3:1][O:2][CH2:3][CH:4]([CH3:20])[O:5][C:6]1[C:7]([NH:19][C:21]([NH2:23])=[S:22])=[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 674866123-(2-Methoxy-1-methyl-ethoxy)-5-phenoxy-pyridine-2-ylamine

Product 1

HCID 86644607[3-(2-Methoxy-1-methyl-ethoxy)-5-phenoxy-pyridin-2-yl]thioureaYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Methoxy-1-methyl-ethoxy)-5-phenoxy-pyridine-2-ylamine (0.28 mmol) is dissolved in THF (4 ml) and 1,1′-thiocarbonyldiimidazole (4 eq.) is added. The reaction solution is stirred 22 hours. 32% NH4OH (20 eq.) is added and stirred 2 hours at room temperature. Water (60 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-1-methyl-ethoxy)-5-phenoxy-pyridin-2-yl]thiourea is obtained as yellow oil in a yield of 70%. HPLC (method C): 1.93 min; LC-MS (method A): 1.85 min, 334.15 (MH+).

Workup

  1. stirringstirred 2 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-d99cd04270ac4dccb5780c11f2ddd52e
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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