Triethylamine → HCID 68387183, compound

HRID 1522761Notes

Reaction equation

HRID 1522761 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[CH:5]=[N:6][OH:7].ClN1C(=O)CCC1=O.[OH:20][CH2:21][C:22](=[CH2:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(N(CC)CC)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[CH2:28][C:22]([CH2:21][OH:20])([C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:7][N:6]=2)[CH:8]=[C:9]([Cl:11])[CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24827Acrylic acid, 2-(hydroxymethyl)-, ethyl esterHCID 31398ChlorosuccinimideHCID 2741423HCID 2741423, compound

Product 1

HCID 68387183HCID 68387183, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.00 g (15.8 mmol) of 3,5-dichlorobenzaldehyde oxime were stirred in 100 ml of DMF together with 2.21 g (16.6 mmol) of N-chlorosuccinimide at RT for 4 h. 3.08 g (23.7 mmol) of ethyl 2-(hydroxymethyl)acrylate and 2.40 g (23.7 mmol) of triethylamine were then added, and the mixture was stirred at RT for 18 h. The reaction solution was concentrated under reduced pressure, and CH2Cl2 and water were then added. The aqueous phase was re-extracted once with CH2Cl2, and the combined organic phases were washed twice with water, dried over Na2SO4, filtered and concentrated. After chromatography on silica gel using n-heptane:ethyl acetate (3:1), the product was obtained. Yield: 3.10 g (62%)

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, and CH2Cl2 and water
  2. additionwere then added
  3. extractionThe aqueous phase was re-extracted once with CH2Cl2
  4. washthe combined organic phases were washed twice with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe product was obtained

Sources & evidence

ORD record
ord-5e4ab40d08724c3fb6149592b871bc99
Source dataset
uspto-grants-2015_07
Patent number
US09078442B2

Reaction notes

Loading…