4'-Mercaptoacetanilide → HCID 13705241, compound

HRID 2301055Notes

Reaction equation

HRID 2301055 reaction equation
[Na].[C:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=1)(=[O:4])[CH3:3].Cl[C:14]1[CH:15]=[CH:16][C:17]([N+:21]([O-:23])=[O:22])=[C:18]([CH:20]=1)[NH2:19]>C(O)C>[NH2:19][C:18]1[CH:20]=[C:14]([S:12][C:9]2[CH:10]=[CH:11][C:6]([NH:5][C:2](=[O:4])[CH3:3])=[CH:7][CH:8]=2)[CH:15]=[CH:16][C:17]=1[N+:21]([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 707774'-MercaptoacetanilideHCID 742185-Chloro-2-nitroanilineHCID 5360545Sodium

Product 1

HCID 13705241HCID 13705241, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (0.269 g) was added to ethanol (20 ml) and the resultant solution was allowed to cool to ambient temperature and 4-acetamidothiophenol (1.94 g) was added. The mixture was stirred for 5 minutes and 5-chloro-2-nitroaniline (2 g) was added. The mixture was then heated under reflux under argon for 3 hours and allowed to cool. The resultant solid was collected by filtration, washed with ethanol then dried to give the title compound (2.46 g) as a solid. NMR: 2.05 (s, 3H), 6.3 (dd, 1H), 6.6 (s, 1H), 7.4 (brs, 2H), 7.5 (d, 2H), 7.7 (d, 2H), 7.9 (d, 1H); MS (ESP+): 304 (M+H)+.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux under argon for 3 hours
  3. temperatureto cool
  4. filtrationThe resultant solid was collected by filtration
  5. washwashed with ethanol
  6. customthen dried

Sources & evidence

ORD record
ord-31f9fcf9074f416f9809bcadce93b270
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

Loading…