Dimethylamine → 3-bromo-7-dimethylsulfamoyl-10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5-one

HRID 1284244Notes

Reaction equation

HRID 1284244 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][C:14]([S:16](F)(=[O:18])=[O:17])=[CH:15][C:8]=3[C:7](=[O:20])[C:6]=2[CH:21]=1.[CH3:22][NH:23][CH3:24]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][C:14]([S:16](=[O:18])(=[O:17])[N:23]([CH3:24])[CH3:22])=[CH:15][C:8]=3[C:7](=[O:20])[C:6]=2[CH:21]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 214121113-bromo-7-fluorosulfonyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

Product 1

HCID 214120943-bromo-7-dimethylsulfamoyl-10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Bromo-7-fluorosulfonyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one (2.5 g., 0.00677 mole) together with 30 ml. of 25% aqueous dimethylamine and 30 ml. of p-dioxane is heated to refluxing for 3 hours. The brown solution is evaporated to dryness under reduced pressure and the residue partitioned between benzene and water. After washing with water, the benzene layer is evaporated to dryness under reduced pressure, leaving 3-bromo-7-dimethylsulfamoyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one as a tan solid, m.p. 142°-145°C., in a yield of 2.1 g. (80%). An analytical sample melts at 146°-148°C. after crystallizations from mixtures of benzene and hexane and from methanol.

Workup

  1. temperatureto refluxing for 3 hours
  2. customThe brown solution is evaporated to dryness under reduced pressure
  3. customthe residue partitioned between benzene and water
  4. washAfter washing with water
  5. customthe benzene layer is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b8089c8ab01c464896d0914aa75b2f3a
Source dataset
uspto-grants-1976_08
Patent number
US03978121

Reaction notes

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