Sodium Hydroxide → 2-(3,5-Dichlorobenzene-1-sulfonyl)-5-(trifluoromethyl)-1,3,4-thiadiazole

HRID 839952

반응식

HRID 839952 반응식
S([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+].[Cl:9][C:10]1[CH:11]=[C:12]([S:17]([O-:19])=[O:18])[CH:13]=[C:14]([Cl:16])[CH:15]=1.Br[C:21]1[S:22][C:23]([C:26]([F:29])([F:28])[F:27])=[N:24][N:25]=1>O.CN(C)C=O>[Cl:16][C:14]1[CH:13]=[C:12]([S:17]([C:21]2[S:22][C:23]([C:26]([F:29])([F:28])[F:27])=[N:24][N:25]=2)(=[O:19])=[O:18])[CH:11]=[C:10]([Cl:9])[CH:15]=1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 128746852-Bromo-5-(trifluoromethyl)-1,3,4-thiadiazoleHCID 179508653,5-Dichlorobenzenesulfinate

생성물 1

HCID 203228832-(3,5-Dichlorobenzene-1-sulfonyl)-5-(trifluoromethyl)-1,3,4-thiadiazole수율 70%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6228Dimethylformamide용매

실험 절차

A solution of 75.6 g (0.6 mole) of analytically pure sodium sulfite in 300 ml of water was pre-warmed to 60°-70° C in a beaker. 122.8 g (0.5 mole) of 3,5-dichlorobenzenesulfochloride, and a solution of 40 g (1 mole) of sodium hydroxide in 200 ml of water were synchronously added dropwise from two dropping funnels in such a way that the pH value (measured with an electrode in the reaction solution) was always between 7 and 9; during the addition the mixture was stirred magnetically. The saline solution of the 3,5-dichlorobenzenesulfinate (about 600 ml) was then diluted with 1.8 liters of dimethylformamide and after adding 116.5 g (0.5 mole) of 2-bromo-5-trifluoromethyl-1,3,4-thiadiazole the whole was stirred for 15 hours at 50° C. The sulfone was precipitated completely by adding ice water and was recrystallized from ethanol. 121 g (70% of theory) of 2-(3',5'-dichlorophenylsulfonyl)-5-trifluoromethyl-1,3,4-thiadiazole of melting point 123° C were obtained.

후처리

  1. additionduring the addition the mixture
  2. stirringwas stirred for 15 hours at 50° C
  3. customThe sulfone was precipitated completely
  4. additionby adding ice water
  5. customwas recrystallized from ethanol

출처 및 근거

ORD 기록
ord-a03dd99102214b99ac881afb4d6bb399
출처 데이터셋
uspto-grants-1978_06
특허 번호
US04097669

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