Pyrrolidine → 1-[2-(4-chlorophenyl)-2-[2,6-dichloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)phenyl]-acetyl]pyrrolidine

HRID 1165849Notes

Reaction equation

HRID 1165849 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].[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>C(#N)C>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([CH:17]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([N:8]3[C:13](=[O:14])[NH:12][C:11](=[O:15])[CH:10]=[N:9]3)=[CH:5][C:4]=2[Cl:16])[C:18]([N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[O:19])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 225573202,6-dichloro-alpha-(4-chlorophenyl)-4(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneacetylchloride

Product 1

HCID 230351901-[2-(4-chlorophenyl)-2-[2,6-dichloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)phenyl]-acetyl]pyrrolidineYield 36.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.28 parts of 2,6-dichloro-α-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneacetylchloride, 4.5 parts of pyrrolidine and 40 parts of acetonitrile was stirred for 17 hours at room temperature. After evaporation in vacuo, the residue was taken up in water and the mixture was acidified with hydrochloric acid. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was dried in vacuo for 48 hours at 110° C., yielding 0.8 parts (36.2%) of 1-[2-(4-chlorophenyl)-2-[2,6-dichloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)phenyl]-acetyl]pyrrolidine; mp. 153.9° C. (intermediate 35).

Workup

  1. customAfter evaporation in vacuo
  2. extractionThe product was extracted with trichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was dried in vacuo for 48 hours at 110° C.

Sources & evidence

ORD record
ord-1f1f8e7140874fd5a813f466271ac52f
Source dataset
uspto-grants-1990_03
Patent number
US04912106

Reaction notes

Loading…