Trifluoroacetic acid → 5-chloro-2-(3-phthalimidomethyl-4H-1,2,4-triazol-4-yl)benzophenone

HRID 1076620Notes

Reaction equation

HRID 1076620 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]([CH:31]=[N:32][NH:33]C(=O)CN1C(=O)C2C(=CC=CC=2)C1=O)[C:17](=O)[CH2:18][N:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]1=[O:29])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]([N:16]2[CH:31]=[N:32][N:33]=[C:17]2[CH2:18][N:19]2[C:20](=[O:29])[C:21]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:26]3[C:27]2=[O:28])=[C:9]([CH:14]=1)[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 854421021,3-dioxo-2-isoindolineacetic acid, [[N-(2-benzoyl-4-chlorophenyl)-1,3-dioxo-2-isoindolineacetamido]methylene]hydrazide

Product 1

HCID 126119465-chloro-2-(3-phthalimidomethyl-4H-1,2,4-triazol-4-yl)benzophenoneYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 1,3-dioxo-2-isoindolineacetic acid, [[N-(2-benzoyl-4-chlorophenyl)-1,3-dioxo-2-isoindolineacetamido]methylene]hydrazide (8.0 g, 0.0123 mole) and toluene (200 ml) is treated with trifluoroacetic acid (0.9 ml) and heated to 100°-110°C for 1.5 hours. The mixture is concentrated in vacuo, and the residue is mixed with cold water and chloroform and made alkaline with aqueous sodium hydroxide. This mixture is extracted with chloroform; the extract is washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on silica gel (400 g) with 1.5% methanol-98.5% chloroform. The product thus obtained is crystallized from methylene chloride-methanol to give: 2.54 g, melting point 228°- 228.5°C. and 0.361 g, melting point 229°-230°C. (53% yield) of 5-chloro-2-[3-(phthalimidomethyl)-4H-1,2,4-triazol-4-yl]benzophenone. The analytical sample has a melting point 229.5°-230.5°.

Workup

  1. temperatureheated to 100°-110°C for 1.5 hours
  2. concentrationThe mixture is concentrated in vacuo
  3. additionthe residue is mixed with cold water and chloroform
  4. extractionThis mixture is extracted with chloroform
  5. washthe extract is washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel (400 g) with 1.5% methanol-98.5% chloroform
  9. customThe product thus obtained
  10. customis crystallized from methylene chloride-methanol
  11. customto give

Sources & evidence

ORD record
ord-88cd367e80cf493b8ca267439ee4c015
Source dataset
uspto-grants-1976_05
Patent number
US03957761

Reaction notes

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