Benzoic Acid → HCID 20535083, compound

HRID 1680931Notes

Reaction equation

HRID 1680931 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(OCC(C)C)=O.[NH2:18][C:19]1[N:24]2[O:25][C:26](=[O:28])[N:27]=[C:23]2[N:22]=[C:21]([N:29]([CH2:33][CH:34]=[CH2:35])[CH2:30][CH:31]=[CH2:32])[N:20]=1>CN(C)C1C=CN=CC=1.C(N(CC)CC)C.C(Cl)Cl>[CH2:33]([N:29]([CH2:30][CH:31]=[CH2:32])[C:21]1[N:20]=[C:19]([NH:18][C:1](=[O:9])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:24]2[O:25][C:26](=[O:28])[N:27]=[C:23]2[N:22]=1)[CH:34]=[CH2:35]

Participants

7

Reactant 3

HCID 243Benzoic AcidHCID 62365Isobutyl chloroformateHCID 20535125HCID 20535125, compound

Product 1

HCID 20535083HCID 20535083, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent2×

Procedure

3.3 g. of benzoic acid are dissolved in 70 ml. of methylene chloride and 2.7 g. of triethylamine. The solution is stirred and treated at 0° C. with 3.5 g. of isobutyl chloroformate in 25 ml. of methylene chloride. The mixture is then stirred at 0° C. for 30 minutes and subsequently at room temperature for 1 hour. The solution is treated with a suspension of 5 g. of 7-amino-5-diallylamino-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-2-one in 200 ml. of methylene chloride, 12.5 ml. of triethylamine and 0.6 g. of 4-dimethylaminopyridine. The mixture obtained is stirred at room temperature for 18 hours and then washed with 100 ml. of water. The organic phase is dried over magnesium sulfate and evaporated under reduced pressure. The residue obtained is purified by column chromatography, there being obtained N-{5-diallylamino-2-oxo-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-7-yl}benzamide having a melting point of 182°-183° C.

Workup

  1. additiontreated at 0° C. with 3.5 g
  2. stirringThe mixture is then stirred at 0° C. for 30 minutes and subsequently at room temperature for 1 hour
  3. additionThe solution is treated with a suspension of 5 g
  4. customThe mixture obtained
  5. stirringis stirred at room temperature for 18 hours
  6. washwashed with 100 ml
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue obtained
  10. customis purified by column chromatography, there

Sources & evidence

ORD record
ord-0cf047f2e0864e1ea8b1d303294396a5
Source dataset
uspto-grants-1981_06
Patent number
US04276417

Reaction notes

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