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

HRID 254384Notes

Reaction equation

HRID 254384 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 530 (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 chromatography (silica gel, chloroform/methanol/ammonium hydroxide, 10:1:0.1, v/v) to afford the free amine 540 (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 chromatography (silica gel, chloroform/methanol/ammonium hydroxide, 10:1:0.1

Sources & evidence

ORD record
ord-c0492839de6f4844aec6d9d5a15423b9
Source dataset
uspto-grants-2011_01
Patent number
US07875619B2

Reaction notes

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