Isobutanol → HCID 22557345, compound

HRID 984043Notes

Reaction equation

HRID 984043 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[CH:8](Cl)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1.N12CCCN=C1CCCCC2.[CH3:36][CH:37]([CH3:40])[CH2:38][OH:39]>>[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)[O:39][CH2:38][CH:37]([CH3:40])[CH3:36]

Participants

4

Reactant 3

HCID 6560IsobutanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 225573573-chloro-4-[chloro(4-chlorophenyl)methyl]phenyl-1,2,4-triazine-3,5(2H,4H)-dione

Product 1

HCID 22557345HCID 22557345, compoundYield 25%

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[3-chloro-4-[chloro(4-chlorophenyl)methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (0.0075 mol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.025 mol) in 2-methylpropanol (25 ml) was stirred for 72 hours at 80° C. The solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97.5/2.5). The pure fractions were collected and the solvent was evaporated. The residue was dried, yielding 0.8 g (25%) of (±)-2-[3-chloro-4-[(4-chloro-phenyl)(2-methylpropoxy)methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (compound 133).

Workup

  1. customThe solvent was evaporated
  2. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97.5/2.5)
  3. customThe pure fractions were collected
  4. customthe solvent was evaporated
  5. customThe residue was dried

Sources & evidence

ORD record
ord-f4ead90a81d84a6f8e65f1b85c6e77dc
Source dataset
uspto-grants-2005_03
Patent number
US06867207B2

Reaction notes

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