Cesium carbonate → 4-[[2-(Diethylamino)ethyl]thio]benzenamine

HRID 1181377Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Cl.[CH2:10]([N:12]([CH2:16][CH3:17])[CH2:13][CH2:14]Cl)[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:10]([N:12]([CH2:16][CH3:17])[CH2:13][CH2:14][S:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)[CH3:11]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-aminothiophenol (23.0 mmol, 2.88 g) in DMF (23 mL) was added 2-(diethylamino)ethyl chloride hydrochloride (11.5 mmol, 1.98 g) and cesium carbonate (34.5 mmol, 11.2 g). The resulting mixture was heated to 60° C. for 3 hours. The solvent was removed by rotary evaporation. The residue was partitioned between dichloromethane and water. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography eluting with 5% methanol in dichloromethane with 1% triethylamine, giving the title compound (1.26 g, 49%). 1H NMR (CDCl3): δ 0.98 (6H, t, J=7.0 Hz), 2.51 (4H, q, J=7.1 Hz), 2.65 (2H, t, J=8.1 Hz), 2.85 (2H, t, J=8.3 Hz), 6.61 (2H, d, J=8.6 Hz), 7.25 (2H, d, J=8.6 Hz). LCMS m/z=225 (m+H+).

Workup

customThe solvent was removed by rotary evaporation
customThe residue was partitioned between dichloromethane and water
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was purified by flash chromatography
washeluting with 5% methanol in dichloromethane with 1% triethylamine

Sources & evidence

ORD record: ord-88be4f47f3524e468bbb3861dbc8797f
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285557B2

Reaction notes

Loading…