Water → HCID 2306777, compound

HRID 1490305Notes

Reaction equation

HRID 1490305 reaction equation
[NH2:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.O>N1C=CC=CC=1>[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17]([NH:1][CH2:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 11952Phenacylamine

Product 1

HCID 2306777HCID 2306777, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-aminoacetophenone (7.0 g, 0.05 mol) in 30 mL of pyridine was added p-toluenesulfonyl chloride (11.8 g, 120 mol %). The reaction mixture was refluxed with stirring for 2 h, cooled to 40°-50° C. and poured in the cold water (150 mL). The mixture was stirred at rt for 1 h, filtered, washed with warm (~40° C.) water and then dried. Recrystallization from EtOH afforded 7.6 g (51%) of the title compound, mp 148.2°-149.3° C. [lit 147°-148° C. (Kemter, G.; Noack, H.; Russ, G. Z. Chem. 1963, 3, 352)]; 1H NMR (CDCl3) δ 11.48 (s, 1H, NH), 7.79 (dd, 1H, J=1.2, J=6.8), 7.72 (d, 1H, J=8.4), 7.67 (d, 1H, J=8.4), 7.44 (t, 1H, J=8), 7.21 (d, 1H, J=8), 7.02 (t, 1H, J=6), 2.55 (s, 3H), 2.36 (s, 3H); 13C NMR (CDCl3) δ 202.37, 143.83, 139.94, 136.47, 134.82, 131.87, 129.57, 127.16, 122.55, 122.18, 118.92, 28.04, 21.42; MS (EI, m/z) 289 (M+).

Workup

  1. temperatureThe reaction mixture was refluxed
  2. temperaturecooled to 40°-50° C.
  3. stirringThe mixture was stirred at rt for 1 h
  4. filtrationfiltered
  5. washwashed
  6. temperaturewith warm (~40° C.) water
  7. customdried
  8. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-85114102540d420e959905e8c3ff0b32
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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