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Hydrochloric Acid → N-(3-(4-methoxypyridin-2-yl)phenyl)thiourea

HRID 1059998
Notes
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Reaction equation

HRID 1059998 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:10]=[C:11]([NH:15][C:16]([NH:18]C(=O)C3C=CC=CC=3)=[S:17])[CH:12]=[CH:13][CH:14]=2)[CH:4]=1.[OH-].[Na+].Cl>CO.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:10]=[C:11]([NH:15][C:16]([NH2:18])=[S:17])[CH:12]=[CH:13][CH:14]=2)[CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18667595N-(3-(4-methoxypyridin-2-yl)phenyl)-N'-benzoylthiourea

Product 1

HCID 18667488N-(3-(4-methoxypyridin-2-yl)phenyl)thioureaYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 962
Water
Solvent

Conditions

Temperature
60 °C

Procedure

To a suspension of N-(3-(4-methoxypyridin-2-yl)phenyl)-N′-benzoylthiourea (429 mg) in methanol (5 ml) was added an aqueous sodium hydroxide solution (1N, 1.42 ml) dropwise. The mixture was stirred at 60° C. for 1 hour and cooled to ambient temperature. The pH was adjusted to 8.0 with 1N hydrochloric acid. The mixture was diluted with water (50 ml) and extracted with dichloromethane-methanol (4:1). The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was triturated with diisopropyl ether, collected by filtration, washed with diisopropyl ether and dried under reduced pressure to give N-(3-(4-methoxypyridin-2-yl)phenyl)thiourea (294 mg).

Workup

  1. temperaturecooled to ambient temperature
  2. extractionextracted with dichloromethane-methanol (4:1)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was triturated with diisopropyl ether
  7. filtrationcollected by filtration
  8. washwashed with diisopropyl ether
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-3d374a08b1144c90a74eb973dc831983
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06521643B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes