Ethyl Acetate → 1-(4-(4-Methoxybenzylthio)-5-bromopyridin-2-yl)-3-benzoylthiourea

HRID 911055Notes

Reaction equation

HRID 911055 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][S:8][C:9]2[C:14]([Br:15])=[CH:13][N:12]=[C:11]([NH2:16])[CH:10]=2)=[CH:5][CH:4]=1.[C:19]([N:27]=[C:28]=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCOC(C)=O>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:28]([NH:27][C:19](=[O:26])[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[S:29])[CH:10]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 68284Benzoyl isothiocyanateHCID 666178114-(4-Methoxybenzylthio)-5-bromopyridin-2-amine

Product 1

HCID 866347701-(4-(4-Methoxybenzylthio)-5-bromopyridin-2-yl)-3-benzoylthioureaYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-methoxybenzylthio)-5-bromopyridin-2-amine (7.45 g, 22.9 mmol) was dissolved in THF (80 mL). Benzoyl isothiocyanate (3.4 ml, 25 mmol) was added, and the reaction was stirred overnight at ambient temperature. The solution was diluted in 9:1 hexanes:EtOAc and stirred for 5 minutes, then filtered and dried to provide the desired product (8.5 g, 76% yield) as a brown solid.

Workup

  1. filtrationfiltered
  2. customdried

Sources & evidence

ORD record
ord-865a476c170c47ff8873028657e29ab9
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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