Acetic Anhydride → HCID 2823103, compound

HRID 399593Notes

Reaction equation

HRID 399593 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

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 trietbylamine (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. temperatureheated at 75°-80° C. for 30 h
  2. temperatureheating
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. temperatureThe filtrate was heated
  6. additiontreated with charcoal
  7. customThe solid was removed by filtration
  8. customthe filtrate evaporated in vacuo
  9. dissolutionThe resulting oil was dissolved in dichloromethane (300 ml)
  10. additiontrietbylamine (8.15 g) added
  11. stirringThe mixture was stirred for 5 hours at room temperature
  12. customthe solvent removed in vacuo
  13. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate
  14. customthe product was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-cdebb3de53fb41469fd525b4998474e9
Source dataset
uspto-grants-1998_10
Patent number
US05821366

Reaction notes

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