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

HRID 2287816Notes

Reaction equation

HRID 2287816 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-3880a1c100ae4352802c72137d1b7a24
Source dataset
uspto-grants-2000_07
Patent number
US06084093

Reaction notes

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