Triethylamine → HCID 57243736, compound

HRID 276003Notes

Reaction equation

HRID 276003 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:12]([NH2:14])=O)=[O:7].C(N(CC)CC)C>ClCCl.O1CCOCC1.[Ti](Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:12]#[N:14])=[O:7]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 57182773HCID 57182773, compound

Product 1

HCID 57243736HCID 57243736, compoundYield 47.3%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Thirty milliliters of 1,4-dioxane were added dropwise to a solution of 1.70 ml of titanium tetrachloride in 4 ml of dichloromethane in a nitrogen atmosphere while being cooled with ice. Then, a solution of 2.70 g of 3-[N-(2chlorobenzyl)acetylamino]-4-nitrobenzamide in 65 ml of 1,4-dioxane was added dropwise thereto. After the mixture was stirred for 15 minutes, 3.14 g of triethylamine were added thereto, and the mixture was stirred for 2 hours while being cooled with ice. After the completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was extracted with ethyl acetate and with water. The organic layer was washed with water, and was dried over magnesium sulfate. Subsequently, the solvent was distilled off under reduced pressure. The residue was purified through column chromatography [200 ml, a mixture of n-hexane and ethyl acetate at a ratio of 4:1] to give 1.21 g of 3-[N-(2-chlorobenzyl)acetylamino]-4-nitrobenznitrile.

Workup

  1. temperaturewhile being cooled with ice
  2. stirringthe mixture was stirred for 2 hours
  3. temperaturewhile being cooled with ice
  4. customAfter the completion of the reaction
  5. distillationthe solvent was distilled off under reduced pressure
  6. extractionthe residue was extracted with ethyl acetate and with water
  7. washThe organic layer was washed with water
  8. dry with materialwas dried over magnesium sulfate
  9. distillationSubsequently, the solvent was distilled off under reduced pressure
  10. customThe residue was purified through column chromatography [200 ml
  11. additiona mixture of n-hexane and ethyl acetate at a ratio of 4:1]

Sources & evidence

ORD record
ord-dff0ccd334064e22924213a4190d43c9
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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