Methyl isothiocyanate → HCID 178479931, compound

HRID 980340Notes

Reaction equation

HRID 980340 reaction equation
[CH3:1][N:2]=[C:3]=[S:4].Cl.[NH2:6][CH2:7][C:8]([C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:13]([OH:20])=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:11]=1)=O>N1C=CC=CC=1>[C:21]([C:12]1[CH:11]=[C:10]([C:8]2[N:2]([CH3:1])[C:3]([SH:4])=[N:6][CH:7]=2)[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:13]=1[OH:20])([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 20222368HCID 20222368, compound

Product 1

HCID 178479931HCID 178479931, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

After stirring a mixture of 100 ml of pyridine, 6 g of methyl isothiocyanate, and 3 g of 4-(2-aminoacetyl)-2,6-di-tert-butylphenol hydrochloride at room temperature for 2 hours, the resulted mixture was maintained at an inside temperature of 80°-90° C. for 1.5 hours. The reaction mixture was concentrated udner reduced pressure and then the residue was extracted with 100 ml of ethyl acetate. The extract was washed with diluted hydrochloric acid, dried, and concentrated under reduced pressure. The residue was recrystallized from ethanol to provide 0.6 g of 5-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-mercapto-1-methylimidazole.

Workup

  1. temperaturethe resulted mixture was maintained at an inside temperature of 80°-90° C. for 1.5 hours
  2. concentrationThe reaction mixture was concentrated udner reduced pressure
  3. extractionthe residue was extracted with 100 ml of ethyl acetate
  4. washThe extract was washed with diluted hydrochloric acid
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-35023d92bee64c13bc4e7ca2197ddc82
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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