Toluene → 3,4-Di(t-butylperoxycarbonyl)-1,2,5-thiadiazole

HRID 1449433

반응식

HRID 1449433 반응식
[S:1]1[N:5]=[C:4]([C:6]([OH:8])=[O:7])[C:3]([C:9]([OH:11])=[O:10])=[N:2]1.N/C(/C#N)=C(\N)/C#N.C1(C)C=CC(S(Cl)(=O)=[O:27])=CC=1.[C:31]([O:35]O)([CH3:34])([CH3:33])[CH3:32].[C:37]1([CH3:43])[CH:42]=CC=C[CH:38]=1>N1C=CC=CC=1.O>[C:31]([O:35][O:10][C:9]([C:3]1[C:4]([C:6]([O:8][O:27][C:37]([CH3:43])([CH3:42])[CH3:38])=[O:7])=[N:5][S:1][N:2]=1)=[O:11])([CH3:34])([CH3:33])[CH3:32]

참가 물질

8

반응물 5

HCID 1140TolueneHCID 6410tert-Butyl hydroperoxideHCID 73974-Toluenesulfonyl chlorideHCID 2700161,2,5-Thiadiazole-3,4-dicarboxylic acid2회HCID 2723951Diaminomaleonitrile

생성물 1

HCID 199776523,4-Di(t-butylperoxycarbonyl)-1,2,5-thiadiazole

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매2회

실험 절차

The preparation described in Warren, J. D., et al, J. Heterocyclic Chem. 16, 1817 (1979) was used to prepare 1,2,5-thiadiazole-3,4-dicarboxylic acid from diaminomaleonitrile. At room temperature, 4.30 g of p-toluenesulfonyl chloride was added to a solution of 0.990 g of 1,2,5-thiadiazole-3,4-dicarboxylic acid in 10 mL of pyridine. The solution was cooled in an ice bath and 1.09 g of t-butylhydroperoxide (90% solution in water) was added. The solution was stirred for one hour during which it was cooled with an ice bath such that the temperature was as low as possible without freezing the pyridine. The solution was then poured into a mixture of water and toluene. The toluene layer was separated and washed twice with a 10% aqueous sodium hydroxide solution. The toluene solution was then dried over sodium sulfate and the solvents removed giving rise to 1.414 g of a yellow liquid. The yellow liquid was purified by column chromatography to give a colorless solid with a melting point of 39°-41° C.; 1H NMR (CDCl3) δ 1.42 (s); IR (coated on a thin polymer film) 1784, 1132, 1019 cm-1 ; ##STR17##

후처리

  1. temperatureThe solution was cooled in an ice bath
  2. temperaturewas cooled with an ice bath such that the temperature
  3. customThe toluene layer was separated
  4. washwashed twice with a 10% aqueous sodium hydroxide solution
  5. dry with materialThe toluene solution was then dried over sodium sulfate
  6. customthe solvents removed

출처 및 근거

ORD 기록
ord-9e8602e786194dc4a165cc74d27d0f81
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05599652

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