2-Aminothiophenol → HCID 12770209, compound

HRID 2294756Notes

Reaction equation

HRID 2294756 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[OH-].[Na+].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1>>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH2:1])=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 87132-AminothiophenolHCID 14798Sodium HydroxideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 12770209HCID 12770209, compoundYield 47%

Procedure

2-Aminothiophenol (25 g, 0.2 mol) was reacted with 16 g sodium hydroxide (0.40 mol) and 34.8 g p-methoxybenzylchoride (0.22 mol) by the method described in Example 24. The mixture was stirred at room temperature for 16 hours. The precipitate was filtered from the reaction mixture, and recrystallised from ethyl acetate to give 23 g of the desired product as a light brown solid (47% yield). 1H NMR (60 MHz, CDCl3): 3.66 (s, 3H), 3.73 (s, 2H), 4.13 (brs, 2H), 6.3-7.3(m, 8H) ppm. TLC (50% ethyl acetate/hexane) Rf 0.80.

Workup

  1. filtrationThe precipitate was filtered from the reaction mixture
  2. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-fd5524887d984456a89bd0a8105b5a54
Source dataset
uspto-grants-1997_11
Patent number
US05690904

Reaction notes

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