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

HRID 1484460ノート

反応式

HRID 1484460 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d64b9ca59a8e4e949e654aa1e85e3f50
出典データセット
uspto-grants-2016_08
特許番号
US09422244B2

反応ノート

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