N-bromobutanimide → [2-[(5-Bromo-3-carbamoyl-2-thienyl)amino]-1,1-dimethyl-2-oxo-ethyl]acetate

HRID 1049865Notes

Reaction equation

HRID 1049865 reaction equation
[C:1]([C:4]1[CH:8]=[CH:7][S:6][C:5]=1[NH:9][C:10](=[O:18])[C:11]([O:14][C:15](=[O:17])[CH3:16])([CH3:13])[CH3:12])(=[O:3])[NH2:2].C1C(=O)N([Br:26])C(=O)C1>CC(O)=O.O>[Br:26][C:7]1[S:6][C:5]([NH:9][C:10](=[O:18])[C:11]([O:14][C:15](=[O:17])[CH3:16])([CH3:12])[CH3:13])=[C:4]([C:1](=[O:3])[NH2:2])[CH:8]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 117717784[2-[(3-Carbamoyl-2-thienyl)amino]-1,1-dimethyl-2-oxo-ethyl]acetate

Product 1

HCID 117717729[2-[(5-Bromo-3-carbamoyl-2-thienyl)amino]-1,1-dimethyl-2-oxo-ethyl]acetate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Intermediate 10 (46.5 g, 172 mmol) is dissolved in AcOH (700 mL). To the resulting suspension, NBS (32.2 g, 181 mmol) is added. The mixture is stirred at room temperature, after which it is evaporated to give a slurry. This slurry is taken up in water to give a suspension that is filtered. Resulting precipitate is dried in the vacuum oven and used as such.

Workup

  1. customafter which it is evaporated
  2. customto give a slurry
  3. customto give a suspension that
  4. filtrationis filtered
  5. customResulting precipitate
  6. customis dried in the vacuum oven

Sources & evidence

ORD record
ord-be3a8bf432934a80b6093a77f65b2733
Source dataset
uspto-grants-2016_07
Patent number
US09382254B2

Reaction notes

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