2,4,6-Trichloroaniline → 5,7-dimethyl-N-(2,4,6-trichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide

HRID 619938ノート

反応式

HRID 619938 の反応式
[Li+].CCC[CH2-].[Cl:6][C:7]1[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10]([Cl:15])[C:8]=1[NH2:9].[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[N:20]2[N:24]=[C:25]([S:27](Cl)(=[O:29])=[O:28])[N:26]=[C:19]2[N:18]=1>CCCCCC.C1COCC1>[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[N:20]2[N:24]=[C:25]([S:27]([NH:9][C:8]3[C:7]([Cl:6])=[CH:13][C:12]([Cl:14])=[CH:11][C:10]=3[Cl:15])(=[O:28])=[O:29])[N:26]=[C:19]2[N:18]=1

参加物

6

反応物 3

HCID 124712,4,6-TrichloroanilineHCID 61028n-Butyl lithiumHCID 6112325,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonyl chloride

生成物 1

HCID 141551475,7-dimethyl-N-(2,4,6-trichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide収率 21.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

A solution (10.7 ml, 17.1 mmol) of 1.60M N-butyllithium in hexane was added to a solution of 3.20 g (16.3 mmol) of 2,4,6-trichloroaniline in 20 ml of dry THF cooled to -78° C. The resultant solution was then allowed to warm to room temperature. This solution was added to a solution of 2.00 g (8.11 mmol) of 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl chloride in 30 ml of dry THF cooled to -10° C. The temperature of the reaction mixture was maintained between -13° C. and -9° C. during to course of the addition. After the addition was complete, the reaction mixture was stirred for 30 minutes and warmed to room temperature. After 1 hour at room temperature, THF was removed from the reaction mixture by evaporation. The residue was triturated with H2O and filtered. The filtrate was treated with charcoal and filtered through celite. The filtrate was washed with Et 2 O, and the aqueous phase was separated and acidified with 3N HCl to precipitate a solid. The solid was collected by filtration, washed with water and dried in vacuo to yield 0.70 g (21%) of the desired product as a tan solid, m.p. >200° C. (decomp.) 1H NMR and IR spectra were consistent with the assigned structure.

後処理

  1. temperatureto warm to room temperature
  2. temperaturecooled to -10° C
  3. temperatureThe temperature of the reaction mixture was maintained between -13° C. and -9° C. during to course of the addition
  4. additionAfter the addition
  5. temperaturewarmed to room temperature
  6. waitAfter 1 hour at room temperature
  7. customTHF was removed from the reaction mixture by evaporation
  8. customThe residue was triturated with H2O
  9. filtrationfiltered
  10. additionThe filtrate was treated with charcoal
  11. filtrationfiltered through celite
  12. washThe filtrate was washed with Et 2 O
  13. customthe aqueous phase was separated
  14. customto precipitate a solid
  15. filtrationThe solid was collected by filtration
  16. washwashed with water
  17. customdried in vacuo

出典と根拠

ORDレコード
ord-4595aa05979247118b762aa8d063d182
出典データセット
uspto-grants-1989_04
特許番号
US04818273

反応ノート

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