Ammonium Chloride → 3-Propyl-6-propylthio-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione

HRID 373233ノート

反応式

HRID 373233 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:21]([S:22][CH2:23][CH2:24][CH3:25])=[CH:20][C:19](=[O:26])[N:18]([CH2:27][CH2:28][CH3:29])[C:17]2=[O:30])=[CH:11][CH:10]=1)#[N:2].[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-].[NH4+]>CN(C)C=O.C(Cl)Cl>[CH2:27]([N:18]1[C:19](=[O:26])[CH:20]=[C:21]([S:22][CH2:23][CH2:24][CH3:25])[N:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]3[NH:33][N:32]=[N:31][N:2]=3)=[CH:14][CH:13]=2)[C:17]1=[O:30])[CH2:28][CH3:29]

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 198115231-(2'-cyanobiphenyl-4-yl)methyl-3-propyl-6-propylthiopyrimidine-2,4(1H,3H)-dione

生成物 1

HCID 1784607433-Propyl-6-propylthio-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione収率 48.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
115 °C

実験手順

A mixture of 1-(2'-cyanobiphenyl-4-yl)methyl-3-propyl-6-propylthiopyrimidine-2,4(1H,3H)-dione (0.77 g), sodium azide (1.8 g) and ammonium chloride (1.48 g) in dimethylformamide (10 ml) was heated at 115° C. for 84 hours. The reaction mixture was diluted with methylene chloride and then the precipitate was filtered. The filtrate was concentrated to dryness in vacuo. The resulting residue was extracted with methylene chloride water. The organic layer was washed with water, dried, and evaporated to dryness. The resulting residue was purified by column chromatography on silica gel to give yellow amorphous powders (0.41 g, 46%).

後処理

  1. filtrationthe precipitate was filtered
  2. concentrationThe filtrate was concentrated to dryness in vacuo
  3. extractionThe resulting residue was extracted with methylene chloride water
  4. washThe organic layer was washed with water
  5. customdried
  6. customevaporated to dryness
  7. customThe resulting residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-8ff225c01e2240aba447f84762656c28
出典データセット
uspto-grants-1992_11
特許番号
US05162326

反応ノート

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