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

HRID 910732Notes

Reaction equation

HRID 910732 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-d92dd28b9b4c455fad25668eb74cb0ee
Source dataset
uspto-grants-2011_09
Patent number
US08022210B2

Reaction notes

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