Triethylamine → HCID 18506134, compound

HRID 1357393Notes

Reaction equation

HRID 1357393 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([C:13]#[N:14])[C:8](=[CH:11][CH:12]=1)[C:9]#[N:10].[N+:19]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26])([O-:21])=[O:20].C(N(CC)CC)C>CC(C)=O.CC(C)=O.CCCCC>[C:13]([C:7]1[CH:6]=[C:5]([CH:12]=[CH:11][C:8]=1[C:9]#[N:10])[O:4][C:3]1[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=1[NH:1][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][CH:30]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=1)#[N:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 18506202HCID 18506202, compound

Product 1

HCID 18506134HCID 18506134, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 23286243HCID 23286243, compoundSolvent

Procedure

A mixture of 4-(2-aminophenoxy)phthalonitrile (0.5 g, 2.1 mmol), 3-nitrobenzoylchloride (0.43 g, 2.3 mmol) and triethylamine (0.54 g, 0.74 ml, 5.3 mmol) in acetone (20 ml) was stirred for 2 hours at room temperature. The mixture was evaporated in vacuo. The crude product was dissolved in methylene chloride (25 ml) and water (25 ml) and 1N hydrochloric acid (1 ml) was added. The water phase was extracted with methylene chloride (2×15 ml). The combined organic phase was dried over magnesium sulphate, filtered and evaporated in vacuo giving 700 mg of the crude product. The product was recystallised in acetone/pentane to give white crystals of N-[2-(3,4-dicyanophenoxy)phenyl]-3-nitrobenzamide (yield: 650 mg (81%)). Mp: 176.5-178.1° C.

Workup

  1. customThe mixture was evaporated in vacuo
  2. dissolutionThe crude product was dissolved in methylene chloride (25 ml)
  3. additionwater (25 ml) and 1N hydrochloric acid (1 ml) was added
  4. extractionThe water phase was extracted with methylene chloride (2×15 ml)
  5. dry with materialThe combined organic phase was dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customgiving 700 mg of the crude product

Sources & evidence

ORD record
ord-527fd9e7596b4034844c5a8672a529f6
Source dataset
uspto-grants-2003_07
Patent number
US06590118B1

Reaction notes

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