Dichloromethane → HCID 59187443, compound

HRID 714650Notes

Reaction equation

HRID 714650 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:12][C:11]([CH3:13])=[N:10][CH:9]=1.[Br:14]N1C(=O)CCC1=O.ClCCl>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:11]1[S:12][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 59187446HCID 59187446, compound

Product 1

HCID 59187443HCID 59187443, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

180 mg (0.86 mmol) of the compound from Example 75A together with 229 mg (1.29 mmol) of N-bromosuccinimide and 14 mg (0.09 mmol) of 2,2′-azobis-2-methylpropanenitrile in 5 ml of carbon tetrachloride were heated under reflux for 8 h. For work-up, the reaction mixture was cooled to RT, and 10 ml of dichloromethane were added. The mixture was washed with 5 ml of water, and the aqueous phase was re-extracted twice with in each case 5 ml of dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified chromatographically [Method 19]. This gave 66 mg (27% of theory) of the target compound.

Workup

  1. temperatureunder reflux for 8 h
  2. washThe mixture was washed with 5 ml of water
  3. extractionthe aqueous phase was re-extracted twice with in each case 5 ml of dichloromethane
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-2929a0d4b4644ce89f9c66fb62c0f5ea
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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