Trifluoroacetic acid → HCID 21494739, compound

HRID 1731103Notes

Reaction equation

HRID 1731103 reaction equation
[Cl:1][C:2]1[CH:49]=[CH:48][CH:47]=[CH:46][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]([CH:28]=[N:29][NH:30][C:31](=O)[CH2:32][CH2:33][N:34]1[C:42](=[O:43])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35]1=[O:44])C(=O)CCN1C(=O)C2C(=CC=CC=2)C1=O)=[O:5].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:49]=[CH:48][CH:47]=[CH:46][C:3]=1[C:4](=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH:28]=[N:29][N:30]=[C:31]1[CH2:32][CH2:33][N:34]1[C:42](=[O:43])[C:41]2=[CH:40][CH:39]=[CH:38][CH:37]=[C:36]2[C:35]1=[O:44]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131710547HCID 131710547, compound

Product 1

HCID 21494739HCID 21494739, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 1,3-dioxo-2-isoindolinepropionic acid, [[N-[2-(o-chlorobenzoyl)phenyl]-1,3-dioxo-2-isoindolinepropionamido]methylene]hydrazide from Preparation 5A is mixed with toluene (165 ml.), treated with trifluoroacetic acid (0.732 ml.) and warmed, under nitrogen, at 100°-110° C. for 1.5 hours. The mixture is concentrated in vacuo and the residue is mixed with cold, dilute sodium bicarbonate and extracted with chloroform. The extract is washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on silica gel (200 g.) with 2% methanol-98% chloroform. The product thus obtained is crystallized to give 2'-chloro-2-[3-(2-phthalimidoethyl)-4H-1,2,4-triazol-4-yl]benzophenone.

Workup

  1. temperaturewarmed, under nitrogen, at 100°-110° C. for 1.5 hours
  2. concentrationThe mixture is concentrated in vacuo
  3. additionthe residue is mixed with cold, dilute sodium bicarbonate
  4. extractionextracted 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 (200 g.) with 2% methanol-98% chloroform
  9. customThe product thus obtained
  10. customis crystallized

Sources & evidence

ORD record
ord-93007679963141d692cf4e7d3eeb6b50
Source dataset
uspto-grants-1976_11
Patent number
US03994940

Reaction notes

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