4-Aminothiophenol → p-Aminophenyl methyl disulfide

HRID 510815

Reaction equation

HRID 510815 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[CH3:9][S:10]S(C)(=O)=O>CO>[CH:2]([NH2:1])([CH3:7])[CH3:3].[CH3:9][S:10][S:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 145104-AminothiophenolHCID 18064S-Methyl methanethiosulfonate

Product 2

HCID 6363IsopropylamineYield 1%HCID 25001884p-Aminophenyl methyl disulfideYield 163.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of p-aminobenzenethiol (125 mg, 1 mmol) in methanol (1 ml) was added MMTS (94 μl, 1 mmol) in a single portion. The reaction was stirred at RT under N2. After 2 hr, the solution was loaded onto an SCX column and eluted with methanol, followed by 1M ammonia in methanol. The basic eluents were concentrated in vacuo to a yellow oil. Chromatography (1:1 hexanes:CH2Cl2 with 1% isopropylamine) yielded 39a (140 mg, 82%) as a pale yellow oil. 1H NMR (250 MHz, CDCl3): δ 7.28 (d, J=8.6 Hz, 2H); 6.54 (d, J=8.6 Hz, 2H); 3.60 (broad s, 2H); 2.34 (s, 3H). Treatment with HCl/ether gave 5 mg of the HCl salt. Biological testing was performed on the acid salt. 1H NMR (400 MHz, d6-DMSO): δ 7.46 (broad s, 2H); 7.05 (broad s, 2H); 2.47 (s, 3H); 2.43 (s, 3H).

Workup

  1. washeluted with methanol
  2. concentrationThe basic eluents were concentrated in vacuo to a yellow oil

Sources & evidence

ORD record
ord-a3ea19eac26b47fd9a66729df72a6098
Source dataset
uspto-grants-2015_08
Patent number
US09096635B2

Linked notes

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