Methanol → N-ethoxycarbonyl-3,4,5,6-tetrahydrophtalimide

HRID 921488Notes

Reaction equation

HRID 921488 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[C:7]1(=[O:17])[NH:11][C:10](=[O:12])[C:9]2[CH2:13][CH2:14][CH2:15][CH2:16][C:8]1=2.C(N(CC)CC)C.CO>CN(C)C=O.C(Cl)(Cl)Cl>[CH2:5]([O:4][C:2]([N:11]1[C:10](=[O:12])[C:9]2[CH2:13][CH2:14][CH2:15][CH2:16][C:8]=2[C:7]1=[O:17])=[O:3])[CH3:6]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 34024Tetrahydrophthalimide

Product 1

HCID 23628598N-ethoxycarbonyl-3,4,5,6-tetrahydrophtalimideYield 42%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl chloroformate (0.38 ml, 4.3 mmol) was added dropwise to a stirred solution of 3,4,5,6-tetrahydrophthalimide (0.5 g, 3.3 mmol) and triethylamine (0.53 ml, 3.8 mmol) in dimethylformamide (6 ml) at 0-5° C. The reaction mixture was allowed to warm to room temperature and stand for 4 h. Methyl alcohol (3 ml) was added, diluted with chloroform (50 ml) and washed with water (3×150 ml). The chloroform solution was dried (Na2SO4) and concentrated in vacuum to give N-ethoxycarbonyl-3,4,5,6-tetrahydrophthalimide (yield 42%).

Workup

  1. washwashed with water (3×150 ml)
  2. dry with materialThe chloroform solution was dried (Na2SO4)
  3. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-eee102e5c03043c2a7d36d9af869ee4e
Source dataset
uspto-grants-2016_03
Patent number
US09273304B2

Reaction notes

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