Hydrochloric Acid → HCID 22557304, compound

HRID 984054Notes

Reaction equation

HRID 984054 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[C:13](=[O:14])[NH:12][C:11](=[O:15])[CH:10]=[N:9]2)[CH:5]=[C:4]([Cl:16])[C:3]=1[CH:17]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[C:18](Cl)=[O:19].[BH4-].[Na+].Cl>O1CCOCC1>[Cl:16][C:4]1[CH:5]=[C:6]([N:8]2[C:13](=[O:14])[NH:12][C:11](=[O:15])[CH:10]=[N:9]2)[CH:7]=[C:2]([Cl:1])[C:3]=1[CH:17]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[CH2:18][OH:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 225573202,6-dichloro-alpha-(4-chlorophenyl)-4(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneacetylchloride

Product 1

HCID 22557304HCID 22557304, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2,6-dichloro-α-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneacetyl chloride (0.188 mol) in 1,4-dioxane (900 ml) was stirred at RT. NaBH4 (36.25 g) was added portionwise over 2.5 hours. The resulting reaction mixture was stirred for 3 hours at RT. The reaction mixture was cooled and acidified till pH 6 with 1 N HCl. The precipitated salts were removed by filtration. The filtrate was washed with water, and the precipitate was filtered off, stirred in DIPE, filtered off and dried, yielding 22.5 g of (±)-2-[3,5-dichloro-4-[1-(4-chlorophenyl)-2-hydroxyethyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (comp. 420). The biphasic filtrate was separated into its layers. The organic layer was dried, filtered and the solvent was evaporated. The residue was purified by HPLC over silica gel (eluent: CH2Cl2/CH3OH 98.5/1.5 and 97/3). The pure fractions were collected and the solvent was evaporated. The residue was stirred in DIPE, filtered off, washed, and dried, yielding 24 g of (±)-2-[3,5-dichloro-4-[1-(4-chlorophenyl)-2-hydroxyethyl]phenyl]-1,2,4-triazin-3,5(2H,4H)-dione (comp. 420).

Workup

  1. customThe resulting reaction mixture
  2. temperatureThe reaction mixture was cooled
  3. customThe precipitated salts were removed by filtration
  4. washThe filtrate was washed with water
  5. filtrationthe precipitate was filtered off
  6. stirringstirred in DIPE
  7. filtrationfiltered off
  8. customdried

Sources & evidence

ORD record
ord-c480b3d8f8194dbe8ff1ffbc9c866a26
Source dataset
uspto-grants-2005_03
Patent number
US06867207B2

Reaction notes

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