Water → HCID 86644603, compound

HRID 1966223Notes

Reaction equation

HRID 1966223 reaction equation
[CH:1]1([O:6][C:7]2[C:8]([NH2:20])=[N:9][CH:10]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:21](N1C=CN=C1)([N:23]1C=CN=C1)=[S:22].[NH4+].[OH-].O>C1COCC1>[CH:1]1([O:6][C:7]2[C:8]([NH:20][C:21]([NH2:23])=[S:22])=[N:9][CH:10]=[C:11]([O:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 68489555HCID 68489555, compound

Product 1

HCID 86644603HCID 86644603, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Cyclopentyloxy-5-phenoxy-pyridine-2-ylamine (0.33 mmol) is dissolved in THF (5 ml) and 1,1′-thiocarbonyldiimidazol (4 eq.) is added. The reaction solution is stirred 19 hours. 32% NH4OH (20 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-Cyclopentyloxy-5-phenoxy-pyridine-2-yl)-thiourea is obtained as brown oil in a yield of 87%; HPLC (method C): 2.13 min; LC-MS (method A): 2.18 min, 330.15 (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-59cd285fa8694ff393ee3b2fab3b9a87
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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