Diethyl Ether → N,N'-Di(p-toluenesulfonyl)-1,2-diamino-1-phenylethane

HRID 363407Notes

Reaction equation

HRID 363407 reaction equation
[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][NH2:4].[OH-:11].[Na+].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.CCO[CH2:27][CH3:28]>O>[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([NH:1][CH:2]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:3][NH:4][S:19]([C:16]2[CH:17]=[CH:18][C:27]([CH3:28])=[CH:14][CH:15]=2)(=[O:20])=[O:11])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 4320111-Phenylethane-1,2-diamine

Product 1

HCID 3974528N,N'-Di(p-toluenesulfonyl)-1,2-diamino-1-phenylethaneYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,2-Diamino-1-phenylethane prepared as in Example 31B (5.0 g, 37.5 mmol) was dissolved in water (110 ml), and sodium hydroxide (3.0 g, 75 mmol) was added in small portions. After stirring for 10 min, p-toluenesulfonyl chloride (14.31 g, 75.1 mmol) was added and stirring was continued for 1 h. Ether (225 ml) was added and the reaction mixture was stirred overnight at room temperature. A white solid precipitated out during this time. The solid was filtered, washed with ether, and dried (13 g). Recrystallization from dichloromethane-hexane gave 12.17 g (73% yield) of a white solid: mp 148°-9° C.; 1H NMR (CDCl3) δ 2.39 (s, 3 H), 2.43 (s, 3 H), 3.19 (m, 2 H), 4.31 (dd, J=12.2, 6.8 Hz, 1 H), 4.77 (t, J=6.6, 1 H), 5.32 (d, J=6.7, 1 H), 6.98 (m, 2 H), 7.19 (m, 5 H), 7.27 (d, J=5.9, 2 H), 7.59 (d, J=8.3 Hz, 2 H), 7.68 (d, J=8.3 Hz, 2 H).

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. stirringthe reaction mixture was stirred overnight at room temperature
  4. customA white solid precipitated out during this time
  5. filtrationThe solid was filtered
  6. washwashed with ether
  7. customdried (13 g)
  8. customRecrystallization from dichloromethane-hexane

Sources & evidence

ORD record
ord-e65e9aa119784891be2b1dd4a3b4aea4
Source dataset
uspto-grants-1999_02
Patent number
US05874421

Reaction notes

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