Tetrahydrofuran → 1-(5-Bromo-3-phenoxypyridin-2-yl)thiourea

HRID 1809547Notes

Reaction equation

HRID 1809547 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[C:18]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][C:16]([Br:26])=[CH:15][N:14]=1)=[S:11])(=O)C1C=CC=CC=1.C1COCC1.[OH-].[Na+]>O>[Br:26][C:16]1[CH:17]=[C:18]([O:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:13]([NH:12][C:10]([NH2:9])=[S:11])=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 866410871-Benzoyl-3-(5-bromo-3-phenoxypyridin-2-yl)thiourea

Product 1

HCID 866314811-(5-Bromo-3-phenoxypyridin-2-yl)thioureaYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 2 L flask was charged with 1-benzoyl-3-(5-bromo-3-phenoxypyridin-2-yl)thiourea (94.3 g, 220 mmol) and THF (900 mL). 2M NaOH (330 mL, 660 mmol) was added and the reaction was heated at reflux overnight. The reaction was cooled to ambient temperature and 300 mL water was added slowly and then the THF was removed in vacuo to afford an aqueous slurry which was filtered, washed with water and dried to give 1-(5-bromo-3-phenoxypyridin-2-yl)thiourea (66.35 g, 93% yield) as a light tan solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux overnight
  3. customthe THF was removed in vacuo
  4. customto afford an aqueous slurry which
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-2c4d19d8b65c41a587ecdfe6098d4560
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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