Acetic Anhydride → HCID 2823103, compound

HRID 1954773Notes

Reaction equation

HRID 1954773 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19][CH3:20])=[O:10].[C:21]([CH2:23][C:24](O)=[O:25])#[N:22].C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1>[NH2:22][C:21]1[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[C:9](=[O:10])[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19][CH3:20])[C:24](=[O:25])[CH:23]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 9740Cyanoacetic acidHCID 23293707HCID 23293707, compound

Product 1

HCID 2823103HCID 2823103, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
77.5 °C

Procedure

1-(2-Methylphenyl)-3-[2-(methylthio)benzyl]urea(23.47 g) and cyanoacetic acid (7.66 g) were ground together and acetic anhydride (23 ml) was added. The mixture was stirred and heated at 75-80° C. for 30 h. Toluene (20 ml) was then added and heating continued for a further 16 hours. The reaction was cooled and filtered. The filtrate was heated to boiling and treated with charcoal. The solid was removed by filtration and the filtrate evaporated in vacuo. The resulting oil was dissolved in dichloromethane (300 ml) and triethylamine (8.15 g) added. The mixture was stirred for 5 hours at room temperature and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate and the product was recrystallised from ethyl acetate. Yield=2.60 g.

Workup

  1. temperatureheating
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. temperatureThe filtrate was heated
  5. additiontreated with charcoal
  6. customThe solid was removed by filtration
  7. customthe filtrate evaporated in vacuo
  8. dissolutionThe resulting oil was dissolved in dichloromethane (300 ml)
  9. additiontriethylamine (8.15 g) added
  10. stirringThe mixture was stirred for 5 hours at room temperature
  11. customthe solvent removed in vacuo
  12. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate
  13. customthe product was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-5e8d11b735824f79898186ddd7e60fd7
Source dataset
uspto-grants-2000_09
Patent number
US06124288

Reaction notes

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