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 1710034ノート

反応式

HRID 1710034 の反応式
[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

参加物

4

反応物 2

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

生成物 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]pyrrolidine収率 36.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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.

出典と根拠

ORDレコード
ord-3ca2f359b12a4114b7366b3c2b4a4f3d
出典データセット
uspto-grants-1990_08
特許番号
US04952570

反応ノート

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