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Pyridine → 5,7-dimethyl-N-(2-acetoxymethyl-6-chlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide

HRID 1031365
ノート
印刷プレビュー

反応式

HRID 1031365 の反応式
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[NH2:13])(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:20][C:21]1[CH:26]=[C:25]([CH3:27])[N:24]2[N:28]=[C:29]([S:31](Cl)(=[O:33])=[O:32])[N:30]=[C:23]2[N:22]=1.S(Cl)(Cl)(=O)=O.[OH-].[Na+]>C(Cl)Cl.C(#N)C>[CH3:20][C:21]1[CH:26]=[C:25]([CH3:27])[N:24]2[N:28]=[C:29]([S:31]([NH:13][C:7]3[C:8]([Cl:12])=[CH:9][CH:10]=[CH:11][C:6]=3[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:32])=[O:33])[N:30]=[C:23]2[N:22]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 24648Sulfuryl chlorideHCID 6112325,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonyl chlorideHCID 141554092-Acetoxymethyl-6-chloroaniline

生成物 1

HCID 141552035,7-dimethyl-N-(2-acetoxymethyl-6-chlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide
収率 13.1%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

A solution of 1.30 gm (6.50 mmol) of 2-amino-3-chlorobenzyl acetate, 4.11 gm (52.0 mmol) of pyridine and 5.0 ml of acetonitrile was treated with 1.61 gm (6.50 mmol) of 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl chloride and the resulting mixture stirred at 25° C. for 120 hours. An additional 0.53 gm (2.2 mmol) of the sulfonyl chloride was added and stirring at 25° C. continued for an additional 24 hours. The mixture was filtered and the filtrate evaporated to provide a brown oil. The oil was then dissolved in 40 ml of methylene chloride and stirred with 25 ml of 0.5M NaOH. After 5 minutes, the aqueous phase was separated, washed with ether and acidified with 3 N HCl. A light brown solid was collected, washed with water, dried and recrystallized from acetonitrile to provide 0.35 gm (13%) of the desired product as a solid, m.p. 214° -217° C., containing approximately 10% of an impurity. IR and 1H NMR spectra were in agreement with the assigned structure.

後処理

  1. stirringstirring at 25° C.
  2. waitcontinued for an additional 24 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated
  5. customto provide a brown oil
  6. waitAfter 5 minutes
  7. customthe aqueous phase was separated
  8. washwashed with ether
  9. customA light brown solid was collected
  10. washwashed with water
  11. customdried
  12. customrecrystallized from acetonitrile

出典と根拠

ORDレコード
ord-a458942d0d7c43449337be557a0b7d8e
出典データセット
uspto-grants-1990_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04954163

反応ノート

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