Water → HCID 21832694, compound

HRID 1740692Notes

Reaction equation

HRID 1740692 reaction equation
O[N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].CN(C)C1CCCCC1.[C:18](Cl)(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[OH2:28]>C1(C)C=CC=CC=1>[C:18]([O:26][CH:4]1[CH2:5][C:6](=[O:7])[NH:2][C:3]1=[O:8])(=[O:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 7415N,N-DimethylcyclohexylamineHCID 8124Octanoyl chlorideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 21832694HCID 21832694, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

115.1 g (1 mol) of N-hydroxysuccinimide are introduced into 600 ml of toluene in a round-bottom flask, and 127.3 g (1 mol) of dimethylcyclohexylamine are added. At 60° C., 162.5 g (1 mol) of octanoyl chloride in 180 ml of toluene are added dropwise. The reaction mixture is stirred at 60° C. for 5 hours. Subsequently water is added and the organic phase is washed with water, concentrated hydrochloric acid, water and sodium bicarbonate solution in this order. The organic phase is dried over sodium sulfate, filtered and concentrated. The crystallized residue is dried at 40° C./100 mbar. 219 g (90%) of octanoyloxysuccinimide are obtained with a purity of 99.5%.

Workup

  1. washthe organic phase is washed with water, concentrated hydrochloric acid, water and sodium bicarbonate solution in this order
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crystallized residue is dried at 40° C./100 mbar

Sources & evidence

ORD record
ord-4797ca81c52c4109b3c696eb05d5d0d3
Source dataset
uspto-grants-1999_10
Patent number
US05972508

Reaction notes

Loading…