Toluene → HCID 86607748, compound

HRID 1767163Notes

Reaction equation

BrC1C=[C:4]([S:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.C([C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1)CCC.C(O[Na])(C)(C)C.[C:27]1(C)[CH:32]=CC=[CH:29][CH:28]=1>C(OCC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:32][CH2:27][CH2:28][CH2:29][N:18]([C:17]1[CH:16]=[CH:15][CH:14]=[CH:20][CH:19]=1)[C:9]1[S:8][CH:4]=[CH:5][C:6]=1[CH3:7]

Participants

Conditions

Temperature: 90 °C

Procedure

2.04 g (10.0 mmol) of 3-bromothioanisole (1), 1.65 g (11.0 mmol) of 4-butylaniline (2), 23 mg (0.025 mmol) of Pd2(dba)3, 42 mg (0.075 mmol) of 1,1′-bis(diphenylphosphino) ferrocene (“DPPF”) and 1.34 g (14 mmol) of t-BuONa were dissolved in 20 mL of toluene. The mixture was stirred for 24 h at 90° C. After cooling to room temperature, it was diluted with 150 mL of diethyl ether and filtered. The solvent was evaporated and the residue was purified by liquid chromatography on silica gel (chloroform/hexane=1:1) to give 2.05 g of N-4-butylphenyl-N-3-methylthiophenylamine (3) (75%). 1H-NMR (400 MHz, CDCl3): δ 7.19 (t, 8 Hz, 1H), 7.15 (m, 2 H), 7.06 (m, 2H), 6.96 (t, J=2 Hz, 1 H), 6.83 (m, 1 H), 6.813 (m, 1H), 2.63 (t, J=7.6 Hz, 2H), 2.49 (s, 3 H), 1.65(m, 2 H), 1.43 (tq, J1,J2=7.2 Hz, 2H), 1.00 (t, J=7.2 Hz, 3H). GC-MS: m/z=273 (M+).

Workup

temperatureAfter cooling to room temperature
filtrationfiltered
customThe solvent was evaporated
customthe residue was purified by liquid chromatography on silica gel (chloroform/hexane=1:1)

Sources & evidence

ORD record: ord-4e5b657f604249009320accbff6bd262
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07232913B2

Reaction notes

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