Methanol → N-ethoxycarbonyl-1,2,3,6-tetrahydrophtalimide

HRID 921489

Reaction equation

HRID 921489 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[C:7]1(=[O:17])[NH:11][C:10](=[O:12])[CH:9]2[CH2:13][CH:14]=[CH:15][CH2:16][CH:8]12.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])[CH:9]2[CH2:13][CH:14]=[CH:15][CH2:16][CH:8]2[C:7]1=[O:17])=[O:3])[CH3:6]

Participants

7

Reactant 4

HCID 887MethanolHCID 68081,2,3,6-TetrahydrophthalimideHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Product 1

HCID 23628680N-ethoxycarbonyl-1,2,3,6-tetrahydrophtalimideYield 82%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl chloroformate (0.18 ml, 1.89 mmol) was added dropwise to a stirred solution of 1,2,3,6-tetrahydrophthalimide (0.22 g, 1.45 mmol) and triethylamine (0.23 ml, 1.67 mmol) in dimethylformamide (2 ml) at 0-5° C. The reaction mixture was allowed to warm to room temperature and stand for 4 h. Methyl alcohol (1 ml) was added, diluted with chloroform (20 ml) and washed with water (3×10 ml). The chloroform solution was dried (Na2SO4) and concentrated in vacuum to give N-ethoxycarbonyl-1,2,3,6-tetrahydrophthalimide (yield 82%).

Workup

  1. washwashed with water (3×10 ml)
  2. dry with materialThe chloroform solution was dried (Na2SO4)
  3. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-e657a01ad393477aad2b02d99c9d7b06
Source dataset
uspto-grants-2016_03
Patent number
US09273304B2

Linked notes

Loading…