Epichlorohydrin → HCID 86662490, compound

HRID 1892033Notes

Reaction equation

HRID 1892033 reaction equation
C(C1OC1)Cl.[CH2:6]([O:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]=1[CH:21]=[N:22][OH:23])[CH:7]1[O:9][CH2:8]1.ClN1C(=O)CCC1=O.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:6]([O:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]=1[C:21]#[N+:22][O-:23])[CH:7]1[O:9][CH2:8]1

Participants

6

Reactant 4

HCID 7835EpichlorohydrinHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 86662489HCID 86662489, compound

Product 1

HCID 86662490HCID 86662490, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

As shown in Chemical Formula 2, 3.00 g (12.3 mmol) of 2-(glycidyloxy)-1-naphthoaldehyde oxime (4) was dissolved in 66 mL of chloroform in an ice bath and thereto, 1.84 g (13.5 mmol) of N-chlorosuccinimide (NCS) was added. While stirring the resultant reaction mixture, 1.63 mL (16.0 mmol) of triethylamine was added to the reaction mixture, followed by stirring the resultant reaction mixture for 6 hours to effect the reaction. Then, the reaction solution was washed with each of 50 mL of pure water and 50 mL of Brine three times, and the organic phase was dried over MgSO4, followed by concentrating the solvent under reduced pressure to obtain 2-(glycidyloxy)-1-naphthonitrile oxide B with a yield of 79%.

Workup

  1. additionwas added to the reaction mixture
  2. stirringby stirring the resultant
  3. customreaction mixture for 6 hours
  4. customthe reaction
  5. washThen, the reaction solution was washed with each of 50 mL of pure water and 50 mL of Brine three times
  6. dry with materialthe organic phase was dried over MgSO4
  7. concentrationby concentrating the solvent under reduced pressure

Sources & evidence

ORD record
ord-55197c48a20e476ead3ddabe272372fa
Source dataset
uspto-grants-2013_08
Patent number
US08507611B2

Reaction notes

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