Isopropanol → HCID 21521117, compound

HRID 918472Notes

Reaction equation

HRID 918472 reaction equation
[C:1]1([C:7]2[O:11][C:10](=[O:12])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:13][C:14]1(C)[CH:28]=[CH:27][C:17]([CH2:18]SC(=S)N(CC)CC)=[CH:16][CH:15]1[CH3:29].[OH-].[Na+].[CH:33](O)(C)C>O>[CH3:33][C:28]1[CH:27]=[C:17]([CH:16]=[C:15]([CH3:29])[C:14]=1[OH:13])[CH2:18][N:9]1[N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:11][C:10]1=[O:12]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 3522082-Phenyl-1,3,4-oxadiazol-2-IN-5-oneHCID 86733764HCID 86733764, compound

Product 1

HCID 21521117HCID 21521117, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

40.5 g of 5-phenyl-1,3,4-oxadiazol-2-one (.25 mol) and 71 g of N,N-diethyl-dithiocarbamic acid (4-hydroxy-3,4-dimethylbenzyl) ester (0.25 mol) are dissolved in 500 ml of isopropanol at 60°C. After dropwise addition of 10 g of sodium hydroxide in 100 ml of water, the mixture is stirred for 9 hours at 60°C. The solvent is then largely evaporated off, the yellow residue is dissolved in acetonitrile, insoluble matter is filtered off and the mother liquor is again evaporated. The residue, which crystallises slowly, is recrystallised from methanol. 3-(3,5-Dimethyl-4-hydroxybenzyl)5-phenyl-1,3,4-oxadiazol-2-one (stabiliser No. 16) of melting point 135°C is thus obtained.

Workup

  1. customThe solvent is then largely evaporated off
  2. dissolutionthe yellow residue is dissolved in acetonitrile
  3. filtrationinsoluble matter is filtered off
  4. customthe mother liquor is again evaporated
  5. customThe residue, which crystallises slowly
  6. customis recrystallised from methanol

Sources & evidence

ORD record
ord-9f63cd4495554fff8c50e74e977c09e5
Source dataset
uspto-grants-1976_07
Patent number
US03971803

Reaction notes

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