Acetic Acid → HCID 54454430, compound

HRID 463549Notes

Reaction equation

HRID 463549 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:16](=[O:17])[C:15](=[O:18])[NH:14][C:13](=[S:19])[N:12]1[CH3:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N+]=[N-])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)(=O)C>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[C:16](=[O:17])[C:15](=[O:18])[N:14]=[C:13]([S:19][CH:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:12]1[CH3:20])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 54058923HCID 54058923, compound

Product 1

HCID 54454430HCID 54454430, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

13.2 g of tetrahydro-2-methyl-5,6-dioxo-3-thioxo-as-triazine-1(2H)-carboxylic acid benzyl ester are dissolved in 500 ml of ethyl acetate and treated with a solution of diphenyldiazomethane in 90 ml of low-boiling petroleum ether. The initially violet solution is left to stand for 40 hours at 25° C., the colour becoming pink. 3 ml of glacial acetic acid are added and, after 1 hour, the mixture is evaporated in vacuo at 40° C. A yellow oil is obtained as the evaporation residue. This is separated by column chromatography on silica gel using benzene, benzene/ethyl acetate (95:5) and benzene/ethyl acetate (90:10) for the elution. The fractions containing the desired substance are combined and evaporated in vacuo at 40° C. After recrystallization from ethanol, there is obtained colourless pure substance of m.p. 90°-92° C.

Workup

  1. waitThe initially violet solution is left
  2. customthe mixture is evaporated in vacuo at 40° C
  3. customA yellow oil is obtained as the evaporation residue
  4. customThis is separated by column chromatography on silica gel
  5. washfor the elution
  6. additionThe fractions containing the desired substance
  7. customevaporated in vacuo at 40° C
  8. customAfter recrystallization from ethanol
  9. customthere is obtained colourless pure substance of m.p. 90°-92° C.

Sources & evidence

ORD record
ord-943bff65dd434b139e518d70cf29ed3a
Source dataset
uspto-grants-1985_05
Patent number
US04520195

Reaction notes

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