N4-Acetylsulfanilamide → HCID 178464663, 화합물

HRID 1484432

반응식

HRID 1484432 반응식
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]

참가 물질

4

반응물 2

HCID 8482N4-AcetylsulfanilamideHCID 53354231HCID 53354231, 화합물

생성물 1

HCID 178464663HCID 178464663, 화합물수율 87%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-95d9982116f6444e8397f412f3ff2ef6
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422244B2

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