N-bromobutanimide → HCID 67994867, compound

HRID 921052Notes

Reaction equation

HRID 921052 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[C:9]([C:13]1[CH:35]=[CH:34][C:16]2[C:17]3[N:25]([C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:27][C:15]=2[N:14]=1)[C:24]1[C:19](=[CH:20][C:21]([CH3:33])=[C:22]([CH3:32])[CH:23]=1)[N:18]=3)([CH3:12])([CH3:11])[CH3:10]>CN(C=O)C>[Br:8][C:20]1[C:21]([CH3:33])=[C:22]([CH3:32])[CH:23]=[C:24]2[C:19]=1[N:18]=[C:17]1[N:25]2[C:26]([C:28]([CH3:29])([CH3:31])[CH3:30])=[CH:27][C:15]2[N:14]=[C:13]([C:9]([CH3:12])([CH3:10])[CH3:11])[CH:35]=[CH:34][C:16]=21

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67995937HCID 67995937, compound

Product 1

HCID 67994867HCID 67994867, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

19.6 g (110 mmol) of NBS are added in portions to a solution, warmed to 100° C., of 36.0 g (100 mmol) of 3,6-di-tert-butyl-8,9-dimethyl-4,6a,11-triazabenzo[a]fluorene, L111, in 300 ml of DMF, and the mixture is subsequently stirred for a further 6 h. The reaction mixture is evaporated to about 150 ml in vacuo, stirred for a further 2 h, the precipitated crystals are filtered off with suction and finally washed twice with 50 ml of methanol each time. Yield: 33.8 g (77 mmol), 77%. Purity: 97% according to 1H-NMR.

Workup

  1. customThe reaction mixture is evaporated to about 150 ml in vacuo
  2. stirringstirred for a further 2 h
  3. filtrationthe precipitated crystals are filtered off with suction
  4. washfinally washed twice with 50 ml of methanol each time

Sources & evidence

ORD record
ord-6efac62e190248f296a511ba0ff3eae0
Source dataset
uspto-grants-2016_03
Patent number
US09273080B2

Reaction notes

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