Beta-Alanine → HCID 53632063, compound

HRID 486106Notes

Reaction equation

HRID 486106 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[CH3:18][N:19]1[CH2:23][C:22](=[O:24])[NH:21][C:20]1=[S:25].NCCC(O)=O.O>C(O)(=O)C>[CH3:4][C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[C:23]2[N:19]([CH3:18])[C:20](=[S:25])[NH:21][C:22]2=[O:24])[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 962WaterHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 33414471-Methyl-2-sulfanylideneimidazolidin-4-one

Product 1

HCID 53632063HCID 53632063, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (19.0 g, 81 mmols), 1-methyl-2-thioxo-4-imidazolidinone (10.6 g, 81 mmols) and beta-alanine (4.7 g, 53 mmols) in acetic acid (150 ml) is stirred under an inert atmosphere and heated to reflux. After 5 hours the mixture is allowed to cool, and is stirred into water (1.5 L). After an hour the product is filtered off, washed three times with water, and dried. Recrystallization from acetonitrile gave the 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-1-methyl-2-thioxo-4-imidazolidinone (17.5 g), mp 242°-244° C.

Workup

  1. temperatureheated to reflux
  2. temperatureto cool
  3. filtrationAfter an hour the product is filtered off
  4. washwashed three times with water
  5. customdried
  6. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-191c25c1d40e4e11b623922bb98b20d3
Source dataset
uspto-grants-1994_03
Patent number
US05290800

Reaction notes

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