Potassium Carbonate → HCID 21072837, compound

HRID 1867343Notes

Reaction equation

HRID 1867343 reaction equation
Br[CH:2]([CH3:5])[C:3]#[N:4].[CH3:6][C:7]1([CH3:18])[O:12][C:11](=[O:13])[NH:10][C:9]2[CH:14]=[CH:15][CH:16]=[CH:17][C:8]1=2.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:6][C:7]1([CH3:18])[O:12][C:11](=[O:13])[N:10]([CH2:5][CH2:2][C:3]#[N:4])[C:9]2[CH:14]=[CH:15][CH:16]=[CH:17][C:8]1=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 306294H-3,1-Benzoxazin-2-one, 1,2-dihydro-4,4-dimethyl-HCID 1405382-Bromopropionitrile2×

Product 1

HCID 21072837HCID 21072837, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10.2 mL (123 mmol) of bromopropionitrile is added dropwise to a solution of 20.0 g (112 mmol) of 4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one and 17.4 g (126 mmol) of potassium carbonate in 250 mL of acetonitrile and the mixture is refluxed overnight. Another 4 mL (48 mmol) of bromopropionitrile is added and the mixture is refluxed for another 2 hours. The solid is suction filtered, the filtrate is evaporated down, and the residue is recrystallized from diisopropylether. White solid. Yield: 22.8 g (88%); mass spectroscopy: [M+H]+=231.

Workup

  1. temperaturethe mixture is refluxed overnight
  2. temperaturethe mixture is refluxed for another 2 hours
  3. filtrationfiltered
  4. customthe filtrate is evaporated down
  5. customthe residue is recrystallized from diisopropylether

Sources & evidence

ORD record
ord-15bfb5c2fc964962b9fec5c03e93bb0e
Source dataset
uspto-grants-2009_12
Patent number
US07632834B2

Reaction notes

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