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

HRID 335125Notes

Reaction equation

HRID 335125 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S: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]([S: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 459260645-Bromo-3-(phenylthio)pyridin-2-amine

Product 1

HCID 866314871-Benzoyl-3-(5-bromo-3-(phenylthio)pyridin-2-yl)thioureaYield 95.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

mL 5-Bromo-3-(phenylthio)pyridin-2-amine (17 g, 60.5 mmol), benzoyl isothiocyanate (9.79 mL, 72.6 mmol), and THF (300 mL) was stirred at 40° C. overnight. Concentrated to half of the original volume and 9:1 hexanes:EtOAc (500 mL) was added. Filtered to afford the title compound (25.7 g, 95.7% yield).

Workup

  1. concentrationConcentrated to half of the original volume and 9:1 hexanes
  2. additionEtOAc (500 mL) was added
  3. filtrationFiltered

Sources & evidence

ORD record
ord-7ba916f7ea504d8382fc812ff7fc61dd
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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