Carbamic acid, ethyl ester → HCID 68034541, compound

HRID 2408352Notes

Reaction equation

HRID 2408352 reaction equation
[C:1](=[O:6])([O:3][CH2:4][CH3:5])[NH2:2].B(F)(F)F.CCOCC.[CH3:16][C:17]([CH3:31])=[CH:18][CH2:19][N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30]>C1(C)C=CC=CC=1>[CH2:4]([O:3][C:1](=[O:6])[NH:2][C:17]([CH3:31])([CH3:16])[CH2:18][CH2:19][N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30])[CH3:5]

Participants

5

Reactant 3

HCID 5641Carbamic acid, ethyl esterHCID 8000Boron trifluoride etherateHCID 96648Phthalimide, N-(3-methyl-2-butenyl)-

Product 1

HCID 68034541HCID 68034541, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

34.2 g of ethyl carbamate are put in the solution in the toluene, 22 mL of BF3.Et2O are added and heating is performed for 1 h 30 mins at 70° C. 11 g of 2-(3-methylbut-2-en-1-yl)-1H-isoindole-1,3-dione are added and heating with reflux is performed for 12 h. After returning to RT, the mixture is dry evaporated and then taken up in an H2O/AcOEt mixture. The organic phase is decanted, washed with a solution saturated with NaCl and then dried on magnesium sulfate. The crude is purified by flash chromatography on silica gel (CH2Cl2/MeOH, 99/1). 5.12 g (yield=31%) of ethyl[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-1,1-dimethylpropyl]-carbamate are obtained as a brown powder used as such.

Workup

  1. additionare added
  2. temperatureheating
  3. temperatureheating
  4. temperaturewith reflux
  5. waitis performed for 12 h
  6. customAfter returning to RT
  7. customthe mixture is dry
  8. customevaporated
  9. customThe organic phase is decanted
  10. washwashed with a solution saturated with NaCl
  11. customdried on magnesium sulfate
  12. customThe crude is purified by flash chromatography on silica gel (CH2Cl2/MeOH, 99/1)

Sources & evidence

ORD record
ord-ff9f806290284191b74c37cdee356513
Source dataset
uspto-grants-2014_08
Patent number
US08815853B2

Reaction notes

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