4-Toluenesulfonyl chloride → N,N'-Di(p-toluenesulfonyl)-1,2-diamino-3-phenylpropane

HRID 363382

반응식

HRID 363382 반응식
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(N([CH2:17][CH3:18])CC)C.[NH2:19][CH2:20][CH:21]([NH2:29])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([NH:19][CH2:20][CH:21]([NH:29][S:7]([C:4]2[CH:5]=[CH:6][C:17]([CH3:18])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 4134343-Phenylpropane-1,2-diamine

생성물 1

HCID 18705612N,N'-Di(p-toluenesulfonyl)-1,2-diamino-3-phenylpropane수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of p-toluenesulfonyl chloride (92.0 g, 0.482 mole) and triethylamine (48.8 g, 0.482 mole) in CH2Cl2 (350 ml) at 0° C. under a dry argon atmosphere was added a solution of 1,2-diamino-3-phenylpropane prepared as in Example 6A (34.5 g, 0.230 mole) in CH2Cl2 (100 ml), maintaining the temperature <10° C. The addition required 1 h. The mixture was allowed to warm to room temperature and was stirred an additional 15 h. The mixture was then poured onto ice (500 g) and the CH2Cl2 layer was separated. The CH2Cl2 layer was washed with 1N HCl, H2O and saturated NaCl solution and was dried (MgSO4). The solvent was removed in vacuo and the resulting yellow oil washed with hexane. The crude product was purified by recrystallization from CH2Cl2 -hexane to give 71.4 g (68% yield) of the product as a crystalline solid: mp 128°-31° C.; 1H NMR (CDCl3) δ 2.42 (s, 3 H), 2.43 (s, 3 H), 2.69 (ABq of dd, γν=44.0 Hz, J=14.0, 6.6 Hz, 2 H), 3.02 (m, 2 H), 3.36 (hex, J=6.6 Hz, 2 H), 4.85 (d, J=6.6 Hz, 1 H), 5.16 (t, J=6.5 Hz, 1 H), 6.87 (m, 2 H), 7.15 (m, 5 H), 7.29 (m, 2 H), 7.50 (m, 2 H), 7.70 (m, 2 H).

후처리

  1. temperaturemaintaining the temperature <10° C
  2. additionThe addition required 1 h
  3. additionThe mixture was then poured onto ice (500 g)
  4. customthe CH2Cl2 layer was separated
  5. washThe CH2Cl2 layer was washed with 1N HCl, H2O and saturated NaCl solution
  6. dry with materialwas dried (MgSO4)
  7. customThe solvent was removed in vacuo
  8. washthe resulting yellow oil washed with hexane
  9. customThe crude product was purified by recrystallization from CH2Cl2 -hexane

출처 및 근거

ORD 기록
ord-2ac5ce29358b4e83ba7c9b3da6a974a3
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05874421

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