Formamide → (+/-)-N-[[2-chloro-4-(4,5-dihydro-3,5-dioxo-1,2,4 triazin-2(3H)-yl)phenyl](4-chlorophenyl)methyl]formamide

HRID 984038Notes

Reaction equation

HRID 984038 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:17]2[C:22](=[O:23])[NH:21][C:20](=[O:24])[CH:19]=[N:18]2)[CH:5]=[CH:6][C:7]=1[C:8](=O)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1.O.[CH:26]([NH2:28])=[O:27]>C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N:17]2[C:22](=[O:23])[NH:21][C:20](=[O:24])[CH:19]=[N:18]2)[CH:5]=[CH:6][C:7]=1[CH:8]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[NH:28][CH:26]=[O:27]

Participants

5

Reactant 3

HCID 713FormamideHCID 962WaterHCID 161969CP 25415

Product 1

HCID 22557358(+/-)-N-[[2-chloro-4-(4,5-dihydro-3,5-dioxo-1,2,4 triazin-2(3H)-yl)phenyl](4-chlorophenyl)methyl]formamideYield 22.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-[3-chloro-4-(4-chlorobenzoyl)phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (0.081 mol) in formic acid (120 ml) and formamide (300 ml) was stirred for 16 hours at 160° C. The reaction mixture was cooled, poured out into water (600 ml) and the resulting precipitate was filtered off and dried. This fraction was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5). The pure fractions were collected and the solvent was evaporated. The residue was stirred in DIPE, filtered off, and dried, yielding 8.78 g (22.5%) of (±)-N-[[2-chloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)phenyl](4-chlorophenyl)methyl]formamide (interm. 64).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe resulting precipitate was filtered off
  3. customdried
  4. customThis fraction was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5)
  5. customThe pure fractions were collected
  6. customthe solvent was evaporated
  7. stirringThe residue was stirred in DIPE
  8. filtrationfiltered off
  9. customdried

Sources & evidence

ORD record
ord-58f9f2c91e4048e1af993c2c5697466e
Source dataset
uspto-grants-2005_03
Patent number
US06867207B2

Reaction notes

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