p-Toluenesulfonic acid → 3-n-Butyl-5-(4-formylbenzylidene) hydantoin

HRID 1733308Notes

Reaction equation

HRID 1733308 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[C:8](=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]3OC=C[O:19]3)=[CH:14][CH:13]=2)[NH:7][C:6]1=[O:23])[CH2:2][CH2:3][CH3:4].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH2:1]([N:5]1[C:9](=[O:10])[C:8](=[CH:11][C:12]2[CH:13]=[CH:14][C:15]([CH:18]=[O:19])=[CH:16][CH:17]=2)[NH:7][C:6]1=[O:23])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 540444323-n-Butyl-5-[4-(1,3-dioxol-2-yl)benzylidene] hydantoin

Product 1

HCID 537932913-n-Butyl-5-(4-formylbenzylidene) hydantoin

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-n-Butyl-5-[4-(1,3-dioxol-2-yl)benzylidene] hydantoin (2.7g; 0.0085 mole) was dissolved in acetone (100 ml.) and stirred overnight at room temperature with p-toluene sulphonic acid (0.5 g.). The hazy solution was evaporated in vacuo and the resultant solid suspended in water (100 ml) and neutralised to pH 7 using dilute sodium bicarbonate solution. The residual solid was filtered off, washed with water and dried to give the title compound m.p. 180° C.

Workup

  1. customThe hazy solution was evaporated in vacuo
  2. filtrationThe residual solid was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-ab7df7569f5d46269542b4377f554922
Source dataset
uspto-grants-1980_12
Patent number
US04241073

Reaction notes

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