Hydrochloric Acid → HCID 13107025, compound

HRID 980336Notes

Reaction equation

HRID 980336 reaction equation
Cl.[NH2:2][CH:3]([CH3:21])[C:4]([C:6]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:9]([OH:16])=[C:8]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:7]=1)=O.C(O)C.Cl.[S-:26][C:27]#[N:28].[Na+]>O>[C:17]([C:8]1[CH:7]=[C:6]([C:4]2[NH:28][C:27](=[S:26])[NH:2][C:3]=2[CH3:21])[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:9]=1[OH:16])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516871Sodium thiocyanateHCID 20222365HCID 20222365, compound

Product 1

HCID 13107025HCID 13107025, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixed solution of 4.3 g of 4-(2-aminopropionyl)-2,6-di-tert-butylphenol hydrochloride, 50 ml of ethanol, and 1.2 ml of concentrated hydrochloric acid was added a solution of 2.2 g of sodium thiocyanate in 4 ml of water at room temperature. After stirring the mixture for 1.5 hours at room temperature and further refluxing the mixture for 2 hours, the solvent was distilled off under reduced pressure. Then, 30 ml of acetic acid was added to the residue and the mixture was refluxed for 2-3 hours. The reaction mixture thus formed was poured into water and the precipitates formed were recovered by filtration. The product was recrysltallized from isopropanol to provide 3.1 g of 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methyl-2-thioxo-4-imidazoline.

Workup

  1. temperaturefurther refluxing the mixture for 2 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThen, 30 ml of acetic acid was added to the residue
  4. temperaturethe mixture was refluxed for 2-3 hours
  5. customThe reaction mixture thus formed
  6. customthe precipitates formed
  7. filtrationwere recovered by filtration

Sources & evidence

ORD record
ord-002b91b1f88a493db121828552552a85
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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