Triethylamine → N'-{2-Chloro-5-[5-(3-chlorothiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-N,N-diethyl-ethane-1,2-diamine

HRID 856981

Reaction equation

HRID 856981 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][C:17]=3[Cl:18])[O:10][N:9]=2)=[CH:4][C:3]=1[NH2:19].[Br:20][CH2:21][CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25].CCN(CC)CC>CCO>[BrH:20].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][C:17]=3[Cl:18])[O:10][N:9]=2)=[CH:4][C:3]=1[NH:19][CH2:21][CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 706082-Bromo-N,N-diethylethanamineHCID 99956372-Chloro-5-[5-(3-chlorothiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenylamine

Product 2

HCID 260Hydrogen BromideHCID 16222811N'-{2-Chloro-5-[5-(3-chlorothiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-N,N-diethyl-ethane-1,2-diamineYield 5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

From 2-chloro-5-[5-(3-chlorothiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenylamine (0.100 g, 0.320 mmol), anhydrous EtOH (1.3 mL), 2-bromo-N,N-diethylethylamine.HBr (0.334 g, 1.28 mmol) and Et3N (0.230 mL, 1.60 mmol) was obtained 0.006 g (5%) of the title compound as a white solid. 1H NMR (acetone-d6): 8.08 (d, 1H, J=5.5 Hz), 7.48–7.37 (m, 3H), 7.34 (d, 1H, J=5.2 Hz), 2.82–2.80 (m, 4H), 2.62–2.58 (m, 4H), 1.07 (t, 6H, J=7.0 Hz).

Sources & evidence

ORD record
ord-cbc27153a8494e6bbe5cc9ffe811ffca
Source dataset
uspto-grants-2006_12
Patent number
US07144876B2

Linked notes

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