Methylamine → S-[4-(4-Aminobutyl)phenyl] dimethylcarbamothioate

HRID 1678300Notes

Reaction equation

HRID 1678300 reaction equation
[CH3:1][N:2]([CH3:27])[C:3]([S:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]2C(=O)C3=CC=CC=C3C2=O)=[CH:8][CH:7]=1)=[O:4].CN>C(O)C>[CH3:27][N:2]([CH3:1])[C:3]([S:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[CH:8][CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59750594HCID 59750594, compound

Product 1

HCID 59750580S-[4-(4-Aminobutyl)phenyl] dimethylcarbamothioateYield 43.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Phthalimide 35 (1.1 g, 2.8 mmol) was dissolved in a solution containing 6.6% methylamine in ethanol (100 mL) and allowed to stir at room temperature overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatotography (silica gel, chloroform/methanol/ammonium hydroxide, 10:1:0.1, v/v) to afford the free amine 36 (0.31 g, 42%) as a white powder. 1H NMR (300 MHz, CD3OD) δ 1.51 (m, 2H), 1.65 (m, 2H), 2.66 (m, 4H), 3.02 (m, 6H), 7.23 (d, 2H), 7.35 (d, 2H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatotography (silica gel, chloroform/methanol/ammonium hydroxide, 10:1:0.1

Sources & evidence

ORD record
ord-78f6ff0309854933a9cb9b3c5245e78c
Source dataset
uspto-grants-2011_08
Patent number
US08008494B2

Reaction notes

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