N-bromobutanimide → tert-butyl (7-bromo-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)carbamate

HRID 1670408Notes

Reaction equation

HRID 1670408 reaction equation
[Br:1]N1C(=O)CCC1=O.[O:9]=[C:10]1[CH:16]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:15][CH2:14][C:13]2[CH:25]=[CH:26][CH:27]=[CH:28][C:12]=2[NH:11]1>CCOC(C)=O>[Br:1][C:26]1[CH:27]=[CH:28][C:12]2[NH:11][C:10](=[O:9])[CH:16]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:23])[CH3:21])[CH2:15][CH2:14][C:13]=2[CH:25]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 13243501tert-butyl N-(2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)carbamate

Product 1

HCID 57655892tert-butyl (7-bromo-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)carbamateYield 203.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

472 mg of N-bromosuccinimide (2.65 mmol) are introduced at AT into a 100 ml round-bottomed flask, with stirring and under an argon atmosphere, containing 40 ml of EtOAc and 0.5 g of 2 (1.8 mmol). The medium is left stirring overnight, and is washed with 40 ml of HCl (1N), 40 ml of saturated aqueous solution of NaHCO3 and 40 ml of water. The organic phase is dried over MgSO4, filtered and then evaporated to dryness. 1.3 g of an oil are obtained, which oil is crystallized from 10 ml of isopropyl ether. After filter-drying, 450 mg of product 10 (white solid) are obtained.

Workup

  1. waitThe medium is left
  2. stirringstirring overnight
  3. washis washed with 40 ml of HCl (1N), 40 ml of saturated aqueous solution of NaHCO3 and 40 ml of water
  4. dry with materialThe organic phase is dried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-01ba691965cd4403b1712313a19d21c5
Source dataset
uspto-grants-2011_08
Patent number
US07994162B2

Reaction notes

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