Lead diacetate trihydrate → N-(4-nitrobenzylmercapto)succinimide

HRID 726418

반응식

HRID 726418 반응식
O.O.O.C([O-])(=O)C.[Pb+2].C([O-])(=O)C.[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][SH:21])=[CH:18][CH:17]=1)([O-:15])=[O:14].Br[N:25]1[C:29](=[O:30])[CH2:28][CH2:27][C:26]1=[O:31]>CO>[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][S:21][N:25]2[C:29](=[O:30])[CH2:28][CH2:27][C:26]2=[O:31])=[CH:18][CH:17]=1)([O-:15])=[O:14]

참가 물질

5

반응물 3

HCID 22456Lead diacetate trihydrateHCID 67184N-bromobutanimideHCID 1936194-Nitrobenzyl mercaptan

생성물 1

HCID 10563677N-(4-nitrobenzylmercapto)succinimide수율 64.9%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
50 °C

실험 절차

Lead (II) acetate trihydrate (0.759 g, 2.0 mmol) and 4-nitrobenzyl mercaptan (0.745 g, 4.4 mmol) were stirred together in methanol (24 cm3) solution at room temperature. After 1 h, the products were filtered and the residue was washed with a small volume of cold methanol. The residue was dried in vacuo over calcium chloride and then suspended in dry acetonitrile (20 cm3). Following the evaporation of the solvent under reduced pressure, the residue was suspended in dry benzene (20 cm3) and the solvent was again evaporated under reduced pressure. Finally, the residue was re-suspended in dry benzene (64 cm3) and N-bromosuccinimide (0.783 g, 4.4 mmol) was added in three portions over a period of 45 min to the stirred suspension at room temperature. The reactants were then heated at 50° C., under an atmosphere of argon, for 14 h. The cooled products were filtered and the filtrate was evaporated under reduced pressure to give a solid. The latter material was crystallized from ethyl acetate--hexane to give N-(4-nitrobenzylmercapto)succinimide 18 (0.76 g, 65%) (Found: C, 49.85; H, 3.8; N, 10.4. C11H10N2O4S requires: C, 49.6; H, 3.8; N, 10.5%), m.p. 146°-148° C.; δH [CDCl3 ] 2.73 (4 H, s), 4.18 (2 H, s), 7.50 (2 H, m), 8.17 (2 H, m); δC [CDCl3 ] 28.4, 40.5, 123.8, 130.3, 141.9, 147.5, 176.2.

후처리

  1. filtrationthe products were filtered
  2. washthe residue was washed with a small volume of cold methanol
  3. dry with materialThe residue was dried in vacuo over calcium chloride
  4. customthe evaporation of the solvent under reduced pressure
  5. customthe solvent was again evaporated under reduced pressure
  6. filtrationThe cooled products were filtered
  7. customthe filtrate was evaporated under reduced pressure
  8. customto give a solid
  9. customThe latter material was crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-9b334624d8024ea2b8ceb3e05794c5f8
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05708161

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