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Triethylamine → [6-(2-Bromoacetyl)-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-4-yl]methyl cyanide

HRID 1295946
Notes
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Reaction equation

HRID 1295946 reaction equation
C(N(CC)CC)C.[C:8]([C:11]1[CH:12]=[C:13]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:14]2[O:19][CH2:18][CH2:17][N:16]([CH2:20][C:21]#[N:22])[C:15]=2[CH:23]=1)(=[O:10])[CH3:9].[Br:28]N1C(=O)CCC1=O.C(OCC)(=O)C>O1CCCC1>[Br:28][CH2:9][C:8]([C:11]1[CH:12]=[C:13]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:14]2[O:19][CH2:18][CH2:17][N:16]([CH2:20][C:21]#[N:22])[C:15]=2[CH:23]=1)=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 22930164(6-acetyl-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-4-yl]methyl cyanide

Product 1

HCID 58910016[6-(2-Bromoacetyl)-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-4-yl]methyl cyanideYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.76 ml, 5.5 mmol) and tert-butyl dimethylsilyltrifluoromethanesulfonate (0.73 g, 5.5 mmol) were added to a solution of [6-acetyl-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-4-yl]methyl cyanide (0.5 g, 1.8 mmol) in tetrahydrofuran (50 ml) while cooling on ice and the mixture was stirred at the same temperature for 30 minutes, after which N-bromosuccinimide (0.49 g, 2.7 mmol) was added and stirring was continued for 30 minutes. Ethyl acetate was added, the reaction mixture was washed with brine and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and then the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (310 mg) as a light yellow solid.

Workup

  1. temperaturewhile cooling on ice
  2. stirringstirring
  3. waitwas continued for 30 minutes
  4. washthe reaction mixture was washed with brine
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4f65d0c3f2bb419db040afc4f4d8c07f
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07244730B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes