Water → HCID 22557413, compound

HRID 984040Notes

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].Cl[CH2:29][CH2:30][Mg].[NH4+].[Cl-].O>C1COCC1>[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)[C:18](=[O:19])[CH2:29][CH3:30]

Participants

Conditions

Temperature: -75 °C

Procedure

A mixture of 2,6-dichloro-α-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4,-triazin-2(3H)-yl)-benzeneacetyl chloride (0.05 mol) in THF (200 ml) was stirred at −75° C. A solution of chloroethyl magnesium (0.1 mol; 2 M/THF) in THF (50 ml) was added dropwise at −75° C. The reaction mixture was stirred for 90 minutes, then the temperature was raised to −20° C. A saturated aqueous NH4Cl solution was added dropwise. Water was added and the product was extracted with CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was filtered over silica gel (eluent: CH2Cl2/CH3OH 98/2). Two fractions were collected and the solvent was evaporated, yielding 3.8 g (±)-2-[3,5-dichloro-4-[1-(4-chlorophenyl)-2-oxobutyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (interm. 69).

Workup

stirringThe reaction mixture was stirred for 90 minutes
temperaturethe temperature was raised to −20° C
extractionthe product was extracted with CH2Cl2
customThe organic layer was separated
customdried
filtrationfiltered
customthe solvent was evaporated
filtrationThe residue was filtered over silica gel (eluent: CH2Cl2/CH3OH 98/2)
customTwo fractions were collected
customthe solvent was evaporated

Sources & evidence

ORD record: ord-44fb76121d9e4729a4a9475b1e117da5
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867207B2

Reaction notes

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