Triethylamine → AG-227/11475014

HRID 1066700Notes

Reaction equation

HRID 1066700 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[CH:9]1([N:15]=[C:16]=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C(N(CC)CC)C>O1CCCC1>[CH:9]1([NH:15][C:16]([O:1][N:2]2[C:6](=[O:7])[CH2:5][CH2:4][C:3]2=[O:8])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18502Cyclohexyl isocyanateHCID 80170N-Hydroxysuccinimide

Product 1

HCID 822832AG-227/11475014Yield 81.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-hydroxysuccinimide (11.5 g, 0.1 mol) was dissolved in 200 g of sufficiently dried tetrahydrofuran. To the solution was added dropwise 12.5 g (0.1 mol) of cyclohexyl isocyanate, and then a catalytic amount of triethylamine was added. After stirring at room temperature overnight, the reaction solution was decolored with active carbon and concentrated. The deposited crystal was filtered and washed with a small amount of ether to obtain 18.0 g of N-(cyclohexylcarbamoyloxy)succinimide represented by the following formula. Yield: 81.5%.

Workup

  1. concentrationconcentrated
  2. filtrationThe deposited crystal was filtered
  3. washwashed with a small amount of ether

Sources & evidence

ORD record
ord-a6bbd29cb1a546639d5648cede5b4f6e
Source dataset
uspto-grants-2001_06
Patent number
US06245478B1

Reaction notes

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