N-bromobutanimide → N-[6-[4-(Cyanomethyl)-1-naphthalenyl]-2-pyridinyl]-2,2-dimethylpropanamide

HRID 1743993Notes

Reaction equation

HRID 1743993 reaction equation
[C:1]([C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH3:24])=[CH:16][CH:15]=2)[N:9]=1)=[O:6])([CH3:4])([CH3:3])[CH3:2].Br[N:26]1C(=O)CC[C:27]1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH2:24][C:27]#[N:26])=[CH:16][CH:15]=2)[N:9]=1)=[O:6])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22236420HCID 22236420, compound

Product 1

HCID 22236389N-[6-[4-(Cyanomethyl)-1-naphthalenyl]-2-pyridinyl]-2,2-dimethylpropanamide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 1.21 g (3.795 mmol) N-t-butylcarbonyl-6-(4-methylnaphthalen-1-yl)-pyridin-2-ylamine, 810 mg (4.554 mmol) N-bromosuccinimide, 35 mL carbon tetrachloride, and 10 mg bis-(1-cyano-1-azo)-cyclohexane. The reaction was heated at reflux for a total of 8 hours as additional portions of initiator were added at 1, 2, and 4 hours. The reaction was cooled, filtered with carbon tetrachloride, and evaporated. The red oil, 2.5 g, was used directly.

Workup

  1. customTo a 100 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was heated
  3. temperatureat reflux for a total of 8 hours as additional portions of initiator
  4. additionwere added at 1, 2, and 4 hours
  5. temperatureThe reaction was cooled
  6. filtrationfiltered with carbon tetrachloride
  7. customevaporated

Sources & evidence

ORD record
ord-2f50edd36aa0466990e4dec0c7eb2304
Source dataset
uspto-grants-2006_03
Patent number
US07012078B2

Reaction notes

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