Benzoyl isothiocyanate → 1-Benzoyl-3-(5-bromo-3-phenoxypyridin-2-yl)thiourea

HRID 1809546Notes

Reaction equation

HRID 1809546 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[C:16]([N:24]=[C:25]=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[C:16]([NH:24][C:25]([NH:8][C:5]1[C:4]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 459261405-Bromo-3-phenoxypyridin-2-amine

Product 1

HCID 866410871-Benzoyl-3-(5-bromo-3-phenoxypyridin-2-yl)thioureaYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 2 L flask was charged with 5-bromo-3-phenoxypyridin-2-amine (64.0 g, 241.4 mmol) and benzoyl isothiocyanate (35.82 mL, 265.6 mmol) in THF (600 mL) and stirred at ambient temperature overnight, then concentrated to about 50 mL. A mixture of Hexanes:EtOAc (9:1) (900 mL) was added with vigorous stirring. The resulting suspension was filtered and the solid was washed with hexanes then dried to afford 1-benzoyl-3-(5-bromo-3-phenoxypyridin-2-yl)thiourea (94.32 g, 91.2% yield) as a yellow solid.

Workup

  1. concentrationconcentrated to about 50 mL
  2. additionA mixture of Hexanes:EtOAc (9:1) (900 mL)
  3. additionwas added with vigorous stirring
  4. filtrationThe resulting suspension was filtered
  5. washthe solid was washed with hexanes
  6. customthen dried

Sources & evidence

ORD record
ord-efc8d176cbea4964abfdf19648580ae1
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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