Benzoyl isothiocyanate → Ethyl 3-(2-(3-benzoylthioureido)-5-bromopyridin-4-yloxy)-4-chlorobenzoate

HRID 911036Notes

Reaction equation

HRID 911036 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=2[Cl:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]([Br:21])=[CH:4][N:3]=1.[C:22]([N:30]=[C:31]=[S:32])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[C:22]([NH:30][C:31](=[S:32])[NH:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=2[Cl:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]([Br:21])=[CH:4][N:3]=1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 66617810Ethyl 3-(2-amino-5-bromopyridin-4-yloxy)-4-chlorobenzoate

Product 1

HCID 86634758Ethyl 3-(2-(3-benzoylthioureido)-5-bromopyridin-4-yloxy)-4-chlorobenzoateYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A flask was charged with ethyl 3-(2-amino-5-bromopyridin-4-yloxy)-4-chlorobenzoate (2.76 g, 7.43 mmol), benzoyl isothiocyanate (1.05 ml, 7.80 mmol) and THF (100 mL). The reaction mixture was stirred at ambient temperature overnight and then concentrated. The residue was purified by silica gel column chromatography using 20% ether in hexanes to give the desired product (1.35 g, 34% yield) as light yellow solid.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-65a12d81dda8438aa19fc2c304257d6e
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

Loading…