Water → [5-(4-Methanesulfonyl-phenoxy)-3-(2-methoxy-ethoxy)-pyridine-2-yl]-thiourea

HRID 1966255Notes

Reaction equation

HRID 1966255 reaction equation
[CH3:1][S:2]([C:5]1[CH:23]=[CH:22][C:8]([O:9][C:10]2[CH:11]=[C:12]([O:17][CH2:18][CH2:19][O:20][CH3:21])[C:13]([NH2:16])=[N:14][CH:15]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C1N=C[N:26]([C:29](N2C=NC=C2)=[S:30])C=1.[NH4+].[OH-].O>C1COCC1>[CH3:1][S:2]([C:5]1[CH:23]=[CH:22][C:8]([O:9][C:10]2[CH:11]=[C:12]([O:17][CH2:18][CH2:19][O:20][CH3:21])[C:13]([NH:16][C:29]([NH2:26])=[S:30])=[N:14][CH:15]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 674864395-(4-Methanesulfonyl-phenoxy)-3-(2-methoxy-ethoxy)-pyridine-2-ylamine

Product 1

HCID 86644610[5-(4-Methanesulfonyl-phenoxy)-3-(2-methoxy-ethoxy)-pyridine-2-yl]-thioureaYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(4-Methanesulfonyl-phenoxy)-3-(2-methoxy-ethoxy)-pyridine-2-ylamine (0.37 mmol) is dissolved in THF (5.5 ml) and 1,1-thiocarbonyldiimidazole (4 eq.) is added. The reaction solution is stirred 3 days. 32% NH4OH (20 eq.) is added and stirred 4 hours at room temperature. 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. [5-(4-Methanesulfonyl-phenoxy)-3-(2-methoxy-ethoxy)pyridine-2-yl]-thiourea is obtained as brown oil in a yield of 75%. HPLC (method C): 1.60 min; LC-MS (method A): 1.37 min, 398.15 (MH+).

Workup

  1. stirringstirred 4 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-cd146b7cef6d4a36b01a504c39f80e08
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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