Isopropyl iodide → HCID 19936597, compound

HRID 36866Notes

Reaction equation

HRID 36866 reaction equation
[H-].[Na+].CC(C)(OC([NH:9][C:10]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[CH:17][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=O)C.I[CH:26]([CH3:28])[CH3:27]>CN(C)C=O>[CH3:27][CH:26]([NH:9][C:10]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[CH:17][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:28]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 12018930Ethyl 2-((tert-butoxycarbonyl)amino)-3-nitrobenzoate

Product 1

HCID 19936597HCID 19936597, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4.8 g (0.12 mol) of a 60% sodium hydride solution are added, at 0° C., under argon, and in portions, to a solution of 34 g (0.11 mol) of ethyl 2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-nitrobenzoate in 100 ml of dimethylformamide. The mixture is left stirring for 20 minutes at 0° C. 55.9 g (0.33 mol) of 2-iodopropane are then added and the mixture is heated at 80° C. for 4 hours and then at room temperature for 48 hours. Hydrolysis is carried out by adding water and extraction is carried out 3 times with ethyl acetate. The organic phase is collected and washed successively with water and with a saturated sodium chloride solution. It is dried and evaporated.

Workup

  1. waitThe mixture is left
  2. temperaturethe mixture is heated at 80° C. for 4 hours
  3. waitat room temperature for 48 hours
  4. customHydrolysis
  5. additionby adding
  6. extractionwater and extraction
  7. customThe organic phase is collected
  8. washwashed successively with water and with a saturated sodium chloride solution
  9. customIt is dried
  10. customevaporated

Sources & evidence

ORD record
ord-f06c21ac8b2c4f9d807003370a4ba72b
Source dataset
uspto-grants-1995_05
Patent number
US05418241

Reaction notes

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