Triethylamine → HCID 45040426, compound

HRID 968090Notes

Reaction equation

HRID 968090 reaction equation
[C:1](Cl)(=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[OH:27][N:28]1[C:32](=[O:33])[CH2:31][CH2:30][C:29]1=[O:34].C(N(CC)CC)C.CCCCCC.C(OCC)C.C(O)(=O)C>ClCCl.CCCCCC>[C:1]([O:27][N:28]1[C:32](=[O:33])[CH2:31][CH2:30][C:29]1=[O:34])(=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80170N-HydroxysuccinimideHCID 11199988Nervonoyl chlorideHCID 21924843Hexane ether acetic acid

Product 1

HCID 45040426HCID 45040426, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A solution of nervonoyl chloride (26 mmol, 10.0 g) in dichloromethane (50 mL) was added drop-wise to a cooled solution (0° C.) of N-hydroxysuccinimide (26 mmol, 3.0 g) and triethylamine (52 mmol, 5.2 g) in dicholoromethane (200 mL). The reaction was stirred for one hour after the addition was complete. TLC analysis (80:18:2 hexane-diethyl ether-acetic acid) indicated complete reaction. The reaction mixture was poured into hexane, filtered and concentrated to dryness. Recrystallisation from ethanol yielded succinimidyl nervonate as a white solid.

Workup

  1. additionafter the addition
  2. customreaction
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-30a155e7b8754ef3b473606ea1bca59a
Source dataset
uspto-grants-2005_10
Patent number
US06956059B2

Reaction notes

Loading…