Hydrogen Sulfide → 3,5-Di-tert-butyl-4-hydroxyphenyl thioacetamide

HRID 1030226Notes

Reaction equation

HRID 1030226 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][C:17]#[N:18])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[SH2:26]>N1C=CC=CC=1>[C:12]([C:9]1[CH:8]=[C:7]([CH2:16][C:17]([NH2:18])=[S:26])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:10]=1[OH:11])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 615568(3,5-Di-tert-butyl-4-hydroxyphenyl)acetonitrile

Product 1

HCID 146278133,5-Di-tert-butyl-4-hydroxyphenyl thioacetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,5-Di-tert-butyl-4-hydroxyphenylacetonitrile (20.0 g) and 11.4 ml of triethylamine were dissolved in 40 ml of pyridine, and hydrogen sulfide was blown into the solution at room temperature over 13 hours. The reaction mixture was concentrated, and the crude product thus obtained was purified by silica gel column chromatography (diethyl ether-hexane =3:7) to give 4.9 g of the desired compound as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude product thus obtained
  3. customwas purified by silica gel column chromatography (diethyl ether-hexane =3:7)

Sources & evidence

ORD record
ord-233302ed76be423e8e7ebd794f843162
Source dataset
uspto-grants-1992_04
Patent number
US05104889

Reaction notes

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