Sodium Hydroxide → 1-(4-(4-Methoxybenzylthio)-5-bromopyridin-2-yl)thiourea

HRID 911056Notes

Reaction equation

HRID 911056 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][S:8][C:9]2[C:14]([Br:15])=[CH:13][N:12]=[C:11]([NH:16][C:17]([NH:19]C(=O)C3C=CC=CC=3)=[S:18])[CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8][C:9]2[C:14]([Br:15])=[CH:13][N:12]=[C:11]([NH:16][C:17]([NH2:19])=[S:18])[CH:10]=2)=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 866347701-(4-(4-Methoxybenzylthio)-5-bromopyridin-2-yl)-3-benzoylthiourea

Product 1

HCID 866347711-(4-(4-Methoxybenzylthio)-5-bromopyridin-2-yl)thioureaYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

1-(4-(4-methoxybenzylthio)-5-bromopyridin-2-yl)-3-benzoylthiourea (8.50 g, 17.4 mmol) was suspended in THF (150 mL). NaOH (116 ml, 348 mmol) was added, and the reaction was stirred at 65° C. overnight. The solution was cooled and filtered, and the solids were washed with cold water. The solids were then triturated in EtOH and filtered to provide the desired product (5.3 g, 79% yield) as a tan solid.

Workup

  1. temperatureThe solution was cooled
  2. filtrationfiltered
  3. washthe solids were washed with cold water
  4. customThe solids were then triturated in EtOH
  5. filtrationfiltered

Sources & evidence

ORD record
ord-4dac2e2829574ed58bebae90fc7f772c
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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