Dichloromethane → HCID 59144031, compound

HRID 2173199Notes

Reaction equation

HRID 2173199 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4]([CH3:11])[CH:3]=1.[Br:12]N1C(=O)CCC1=O.ClCCl>ClC(Cl)(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4]([CH2:11][Br:12])[CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 53438912Methyl 5-bromo-3-methylthiophene-2-carboxylate

Product 1

HCID 59144031HCID 59144031, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

In a 100 mL round bottom flask, methyl 5-bromo-3-methylthiophene-2-carboxylate (1.50 g, 6.38 mmol) was dissolved in tetrachloromethane (30 mL). To above solution was added 1-bromopyrrolidine-2,5-dione (1.14 g, 6.38 mmol, 1.0 eq) and diphenylperoxyanhydride (0.155 g, 0.638 mmol, 0.1 eq). The reaction was stirred at 90° C. for 18 hr. To above reaction was added dichloromethane (30 mL), washed with aqueous sodium bicarbonate, brine and water. The organic phase was dried over MgSO4, filtered and concentrated. The crude was used in next step without purification. LC-MS (IE, m/z): 337.4 [M+N]+.

Workup

  1. customTo above reaction
  2. washwashed with aqueous sodium bicarbonate, brine and water
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was used in next step without purification

Sources & evidence

ORD record
ord-992403816980471c944d15d5b797d91b
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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