3-Bromothiophene → HCID 66351280, compound

HRID 1944768Notes

Reaction equation

Br[C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[CH2:7]([NH2:19])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.CN(C)CCO>[CH2:7]([NH:19][C:2]1[CH:6]=[CH:5][S:4][CH:3]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 3-bromothiophene (7.20 g, 44.16 mmol), dodecylamine (12.28 g, 166.24 mmol), Cu (0.14 g, 2.21 mmol), CuI (0.42 g, 2.21 mmol), K3PO4 (18.75 g, 88.32 mmol), and N,N-dimethylethanolamine (60 mL) is purged with N2. The reaction mixture is then stirred for 2 days at 90° C. under nitrogen. The reaction mixture is quenched with water and extracted with diethyl ether followed by washing with brine. The organic layer is dried over Na2SO4. The crude compound is purified by column chromatography on silica gel with 0-5% ethyl acetate in hexane as eluent to give 3-dodecylaminothiophene (6a) as a brown solid (5.75 g, 49%). 1H-NMR (400 MHz) ppm 7.11 (dd, 1H, J=3.0 Hz, J=5.2 Hz), 6.58 (dd, 1H, J=1.5 Hz, J=5.1 Hz), 5.88 (dd, 1H, J=1.5 Hz, J=3.0 Hz), 3.02 (t, 2H, J=7.1 Hz), 1.58 (m, 2H), 1.35 (m, 18H), 0.86 (t, 3H, J=6.8 Hz).

Workup

customis purged with N2
customThe reaction mixture is quenched with water
extractionextracted with diethyl ether
washby washing with brine
dry with materialThe organic layer is dried over Na2SO4
customThe crude compound is purified by column chromatography on silica gel with 0-5% ethyl acetate in hexane as eluent

Sources & evidence

ORD record: ord-59f8bd7ee08a43e7b5c38dae27f6a0d1
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394919B2

Reaction notes

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