N-bromobutanimide → HCID 12813977, compound

HRID 1579150Notes

Reaction equation

HRID 1579150 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][N:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:14](=[O:21])[CH2:13][C:12]2[CH:22]=[CH:23][CH:24]=[CH:25][C:11]1=2>CN(C)C=O>[Br:8][C:19]1[CH:18]=[CH:17][C:16]2[N:10]([CH3:9])[C:11]3[CH:25]=[CH:24][CH:23]=[CH:22][C:12]=3[CH2:13][C:14](=[O:21])[C:15]=2[CH:20]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 786205,11-Dihydro-5-methyl-10H-dibenz(b,f)azepin-10-one

Product 1

HCID 12813977HCID 12813977, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

22.81 g of N-bromosuccimide were added over 15 minutes at room temperature to a solution of 25 g of 5-methyl-10,11-dihydro [5H] dibenzo (b,f) azepine-10-one in 250 ml of dimethylformamide under a nitrogen atmosphere and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was poured into 2 liters of ice water and was extracted with ether. The ether extracts were washed with water, dried over magnesium sulfate and evaporated to dryness to obtain 34 g of 2-bromo-5-methyl-10,11-dihydro [5H] dibenzo (b,f) azepine-11-one. The product was dissolved in 100 ml of refluxing ethyl acetate and the solution was filtered hot and concentrated to the start of crystallization. The mixture was iced for 30 minutes and vacuum filtered. The recovered precipitate was washed with ethyl acetate and dried under reduced pressure to obtain 29.5 g of the said product in the form of pale yellow crystals melting at 128°-129°C.

Workup

  1. extractionwas extracted with ether
  2. washThe ether extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-802e3c954f5a474aa0b1f6ee4fa0b522
Source dataset
uspto-grants-1976_01
Patent number
US03931151

Reaction notes

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