5-Chlorothiophene-2-Sulfonamide → 5-Chloro-thiophene-2-sulfonic acid amino-(4,4-dimethyl-4,5-dihydro-pyrazol-1-yl)-methyleneamide

HRID 1484460노트

반응식

HRID 1484460 반응식
CS[C:3]([N:5]1[CH2:9][C:8]([CH3:11])([CH3:10])[CH:7]=[N:6]1)=[NH:4].[Cl:12][C:13]1[S:17][C:16]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:15][CH:14]=1>C(#N)C>[NH2:4][C:3]([N:5]1[CH2:9][C:8]([CH3:11])([CH3:10])[CH:7]=[N:6]1)=[N:21][S:18]([C:16]1[S:17][C:13]([Cl:12])=[CH:14][CH:15]=1)(=[O:20])=[O:19]

참가 물질

4

반응물 2

HCID 12413015-Chlorothiophene-2-SulfonamideHCID 673594724,4-Dimethyl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester

생성물 1

HCID 699280035-Chloro-thiophene-2-sulfonic acid amino-(4,4-dimethyl-4,5-dihydro-pyrazol-1-yl)-methyleneamide수율 80%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1.0 g (1 mol equiv.) 4,4-Dimethyl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester and 1.21 g (1.05 mol equiv.) 5-chloro-thiophene-2-sulfonic acid amide were added to 10 mL acetonitrile. The reaction mixture was refluxed overnight, and volatiles were removed under reduced pressure. The residue was taken up in ethyl acetate and extracted with 2N NaOH. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. Purification by flash chromatography on silica gel (Et2O:PA=2:1) afforded 1.58 g (80%) 5-chloro-thiophene-2-sulfonic acid amino-(4,4-dimethyl-4,5-dihydro-pyrazol-1-yl)-methyleneamide. 1H NMR (400 MHz, CDCl3) δ 1.25 (s, 6H), 3.63 (s, 2H), 6.00-6.50 (br.s., 1H), 6.79 (s, 1H), 6.85 (d, J=4.0 Hz, 1H), 7.10-7.35 (br.s., 1H), 7.37 (d, J=4.0 Hz, 1H).

후처리

  1. temperatureThe reaction mixture was refluxed overnight
  2. customvolatiles were removed under reduced pressure
  3. extractionextracted with 2N NaOH
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification by flash chromatography on silica gel (Et2O:PA=2:1)

출처 및 근거

ORD 기록
ord-d64b9ca59a8e4e949e654aa1e85e3f50
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422244B2

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