Sulfur trioxide → N-(1,3-dioxoisoindol-2-yl)benzamide

HRID 1658456Notes

Reaction equation

HRID 1658456 reaction equation
S(=O)(=O)=O.[C:5]([NH:13][NH:14][C:15](=[O:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([OH:24])=O)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN(C)C=O>[C:15]1(=[O:25])[N:14]([NH:13][C:5](=[O:12])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:22](=[O:24])[C:17]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:16]12

Participants

4

Reactant 2

HCID 24682Sulfur trioxideHCID 2787565HCID 2787565, compound

Product 1

HCID 690733N-(1,3-dioxoisoindol-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Dry dimethylformamide (D.M.F.) (300 ml) was cooled in an ice-bath and with stirring treated dropwise with sulphur trioxide (SO3) (100 ml) such that the temperature did not exceed 5°. With continued ice-bath cooling the D.M.F./SO3 complex was treated dropwise with a solution of 1-benzoyl-2-(2-carboxybenzoyl)-hydrazine (148.5 g, 0.52 mole) dissolved in dry D.M.F. (200 ml). After the addition, the reaction was stirred for a further 1/2 hour at 0° and then for several hours with the ice-bath removed. The reaction mixture was poured into water (2 l) and allowed to stand until the paste which separated became hard. The crude product was collected on a filter, washed well with water, then air dried, wt. 143 g. This crude product was stirred into a solution of sodium bicarbonate (150 g) in water (1.4 l) till all effervescence had ceased. Undissolved material was collected on a filter, washed with water and air dried, 26 g (18%). Recrystallization from methanol gave white crystals of N-phthalimidobenzamide, (IV) (R1 =H), M.P. 215°-218°.

Workup

  1. customdid not exceed 5°
  2. additionAfter the addition
  3. stirringthe reaction was stirred for a further 1/2 hour at 0°
  4. customfor several hours with the ice-bath removed
  5. additionThe reaction mixture was poured into water (2 l)
  6. customseparated
  7. customThe crude product was collected on a filter
  8. washwashed well with water
  9. customair dried
  10. stirringThis crude product was stirred into a solution of sodium bicarbonate (150 g) in water (1.4 l) till all effervescence
  11. customwas collected on a filter
  12. washwashed with water and air
  13. customdried
  14. customRecrystallization from methanol

Sources & evidence

ORD record
ord-6e8a38a8fbf6413a90ebe0a1a6f6e9da
Source dataset
uspto-grants-1976_06
Patent number
US03964896

Reaction notes

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