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Cesium carbonate → 4-[4-Methyl-2-([1,3,4]thiadiazol-2-ylamino)-thiazol-5-yl]-benzenesulfonamide

HRID 908157
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HRID 908157 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].C[C:8]1[S:12][C:11]([NH2:13])=[N:10][N:9]=1.Cl[C:15]1[S:16][C:17]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)=[C:18]([CH3:20])[N:19]=1.C(OCC)(=O)C.CO>CC(N(C)C)=O>[CH3:20][C:18]1[N:19]=[C:15]([NH:13][C:11]2[S:12][CH:8]=[N:9][N:10]=2)[S:16][C:17]=1[C:21]1[CH:22]=[CH:23][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:25][CH:26]=1
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참가 물질

6

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HCID 10796Cesium carbonateHCID 669491,3,4-Thiadiazole, 2-amino-5-methyl-2회HCID 21584119Ethylacetate methanolHCID 673920414-(2-Chloro-4-methyl-thiazol-5-yl)-benzenesulfonamide

생성물 1

HCID 866062114-[4-Methyl-2-([1,3,4]thiadiazol-2-ylamino)-thiazol-5-yl]-benzenesulfonamide수율 9.5%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
110 °C

실험 절차

Caesium carbonate (0.08 g, 0.24 mmol) and 5-methyl-[1,3,4]thiadiazol-2-ylamine (0.031 g, 0.27 mmol) are added to a solution of 4-(2-chloro-4-methyl-thiazol-5-yl)-benzenesulfonamide (25d) (0.07 g, 0.24 mmol) in dimethylacetamide (2 ml). The mixture is heated with stirring at 110° C. for 18 hours. After adding more 5-methyl-[1,3,4]thiadiazol-2-ylamine (0.056 g, 0.49 mmol) heating is continued at 130° C. for an additional 8 hours. The solvent is removed and the product is purified by chromatography on silica eluting with ethyl acetate to give an orange solid. Trituration with ethyl acetate-methanol affords the title compound as a yellow solid (0.0081 g)

후처리

  1. temperatureThe mixture is heated
  2. temperatureheating
  3. waitis continued at 130° C. for an additional 8 hours
  4. customThe solvent is removed
  5. customthe product is purified by chromatography on silica eluting with ethyl acetate
  6. customto give an orange solid

출처 및 근거

ORD 기록
ord-932366fa9fdf4f6d94af2f0ec1f72f89
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08017608B2

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