Pyridine → Benzeneacetamide

HRID 1584067Notes

Reaction equation

HRID 1584067 reaction equation
[S].[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]=[CH:9][C:10]1C=CC=CC=1.C(C1C=C(O)C(=CC=1)[OH:24])(C)(C)C>N>[C:5]1([CH2:6][C:7]([NH2:2])=[O:24])[CH:10]=[CH:9][CH:8]=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 73814-tert-ButylcatecholHCID 7501StyreneHCID 5362487Sulfur

Product 1

HCID 7680Benzeneacetamide

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of sulfur (15 g, 58.4 mmol), pyridine (15 mL, 14.67 g, 185.5 mmol), aqueous ammonia (28%; 20 mL), styrene (8.66 g, 83.3 mmol) and 4-t-butylcatechol (0.23 g, 1.69 mmol) was heated to 170° C. for 10 minutes then rapidly cooled using the cold-finger. Phenylacetamide was obtained upon workup (5.7 g, 51%). No impurities were detected in the 1H n.m.r. or 13C n.m.r. spectra.

Workup

  1. temperaturethen rapidly cooled

Sources & evidence

ORD record
ord-c0ec036dcbe54e5f912ff90a3e3caf36
Source dataset
uspto-grants-1999_08
Patent number
US05932075

Reaction notes

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