Methanol → HCID 10607267, compound

HRID 921491Notes

Reaction equation

HRID 921491 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[C:7]1(=[O:13])[NH:11][C:10](=[O:12])[CH2:9][CH2:8]1.C(N(CC)CC)C.CO>CN(C)C=O.C(Cl)(Cl)Cl>[CH2:5]([O:4][C:2]([N:11]1[C:7](=[O:13])[CH2:8][CH2:9][C:10]1=[O:12])=[O:3])[CH3:6]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 11439Succinimide

Product 1

HCID 10607267HCID 10607267, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl chloroformate (1.24 ml, 13.1 mmol) was added dropwise to a stirred solution of succinimide (1.0 g, 10 mmol) and triethylamine (1.6 ml, 11.5 mmol) in dimethylformamide (10 ml) at 0-5° C. The reaction mixture was allowed to warm to room temperature and stand for 3 h. Methyl alcohol (1 ml) was added, diluted with chloroform (40 ml) and washed with water (2×20 ml). The chloroform solution was dried (Na2SO4) and concentrated in vacuum to give N-ethoxycarbonyl-succinimide (yield 60%).

Workup

  1. washwashed with water (2×20 ml)
  2. dry with materialThe chloroform solution was dried (Na2SO4)
  3. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-f0297179faab4db9be069e854dbe3484
Source dataset
uspto-grants-2016_03
Patent number
US09273304B2

Reaction notes

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