N-bromobutanimide → HCID 59001428, compound

HRID 1594223Notes

Reaction equation

HRID 1594223 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([NH:11][C:12]([NH:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[S:13])[N:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:7]=1)=[O:5])[CH3:2].BrN1C(=O)CCC1=O>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[S:13][C:12]([NH:14][C:15](=[O:22])[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:11][C:9]=2[N:8]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59001357HCID 59001357, compound

Product 1

HCID 59001428HCID 59001428, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1-Phenyl-5-[3-benzoyl-thioureido]-1H-pyrazole-3-carboxylic acid ethyl ester (500 mg, 1.26 mmol) was dissolved in 25 ml anhydrous CHCl3. N-Bromosuccinimide (225 mg, 1.26 mmol) was added portion wise in 5-10 minutes at 0° C. The reaction mixture was stirred at room temperature for 2 hours. After the completion of reaction, 100 ml of CHCl3 was added to the reaction flask and the organic layer was washed with NaHCO3 (2×30 ml), followed by brine, and dried over Na2SO4. Removal of the solvent gave product, which was sufficiently pure (>95%) for use in the following step. The crude product was further purified by SiO2 column to give 450 mg of title compound (Yield: 91%).

Workup

  1. additionwas added to the reaction flask
  2. washthe organic layer was washed with NaHCO3 (2×30 ml)
  3. dry with materialdried over Na2SO4
  4. customRemoval of the solvent
  5. customgave product, which
  6. customThe crude product was further purified by SiO2 column

Sources & evidence

ORD record
ord-48b924e3e57c4a078f5623d6e227bddc
Source dataset
uspto-grants-2007_11
Patent number
US07300949B2

Reaction notes

Loading…