Water → (3-Cyclopentylmethoxy-5-phenoxy-pyridine-2-yl)-thiourea

HRID 1966244Notes

Reaction equation

HRID 1966244 reaction equation
[CH:1]1([CH2:6][O:7][C:8]2[C:9]([NH2:21])=[N:10][CH:11]=[C:12]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:13]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:22](N1C=CN=C1)([N:24]1C=CN=C1)=[S:23].[NH4+].[OH-].O>C1COCC1>[CH:1]1([CH2:6][O:7][C:8]2[C:9]([NH:21][C:22]([NH2:24])=[S:23])=[N:10][CH:11]=[C:12]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 684895913-Cyclopentylmethoxy-5-phenoxy-pyridine-2-ylamine

Product 1

HCID 86644608(3-Cyclopentylmethoxy-5-phenoxy-pyridine-2-yl)-thioureaYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Cyclopentylmethoxy-5-phenoxy-pyridine-2-ylamine (0.97 mmol) is dissolved in THF (10 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 (250 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-Cyclopentylmethoxy-5-phenoxy-pyridine-2-yl)-thiourea is obtained as yellow solid in a yield of 70%. HPLC (method C): 2.24 min; LC-MS (method A): 2.372 min, 344.15 (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-0ea0b9bb80d84e83be2e483c6899de17
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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