N4-Acetylsulfanilamide → HCID 178464663、化合物

HRID 1484432

反応式

HRID 1484432 の反応式
CS[C:3]([N:7]1[N:11]=[CH:10][C:9]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:8]1)=[N:4][CH2:5][CH3:6].[C:16]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1)(=[O:18])[CH3:17]>C(#N)C>[CH2:8]1[C:9]2([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH:10]=[N:11][N:7]1[C:3](=[N:29][S:26]([C:23]1[CH:22]=[CH:21][C:20]([NH:19][C:16](=[O:18])[CH3:17])=[CH:25][CH:24]=1)(=[O:27])=[O:28])[NH:4][CH2:5][CH3:6]

参加物

4

反応物 2

HCID 8482N4-AcetylsulfanilamideHCID 53354231HCID 53354231、化合物

生成物 1

HCID 178464663HCID 178464663、化合物収率 87%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

157 mg (1 mol equiv.) N-Ethyl-2,3-diaza-spiro[4.4]non-3-ene-2-carboximidothioic acid methyl ester and 157 mg (1.05 mol equiv.) 4-acetamidobenzenesulfonamide were taken up in 5 mL acetonitrile. The reaction mixture was refluxed overnight under magnetic stirring and volatiles were removed in vacuo. 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 (ethyl acetate) afforded 236 mg (87%) of N-(4-{[(2,3-diaza-spiro[4.4]non-3-en-2-yl)-ethylamino-methylene]-sulfamoyl}-phenyl)-acetamide. 1H NMR (400 MHz, CDCl3) δ 1.14 (t, J=7.2 Hz, 3H), 1.62-1.83 (m, 8H), 2.20 (s, 3H), 3.43-3.51 (m, 2H), 3.80 (s, 2H), 6.80 (s, 1H), 6.87 (br.s., 1H), 7.56 (d, J=8.8 Hz, 2H), 7.77 (br.s., 1H), 7.83 (d, J=8.8 Hz, 2H).

後処理

  1. temperatureThe reaction mixture was refluxed overnight
  2. customvolatiles were removed in vacuo
  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 (ethyl acetate)

出典と根拠

ORDレコード
ord-95d9982116f6444e8397f412f3ff2ef6
出典データセット
uspto-grants-2016_08
特許番号
US09422244B2

関連ノート

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