Dabco → HCID 66625069, compound
Reaction equation
[N+:1]([C:4]1[S:8][C:7]([CH:9]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1N2CCN(CC2)C1.[CH2:19]([O:21][C:22]([C:24]1[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:27]([N:34]=[CH:35][C:36]2[S:37][C:38]([N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])=[CH:39][CH:40]=2)[S:26][C:25]=1[NH2:46])=[O:23])[CH3:20]>C1(C)C=CC=CC=1.Cl[Ti](Cl)(Cl)Cl>[CH2:32]([O:31][C:29]([C:28]1[C:24]([C:22]([O:21][CH2:19][CH3:20])=[O:23])=[C:25]([N:46]=[CH:9][C:7]2[S:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[S:26][C:27]=1[N:34]=[CH:35][C:36]1[S:37][C:38]([N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])=[CH:39][CH:40]=1)=[O:30])[CH3:33]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
5-Nitrothiophene-2-carbaldehyde (23 mg) was mixed in toluene under nitrogen at 0° C. with DABCO (16 mg), TiCl4 in solution in toluene (146 μL) and 2-amino-5-[(5-diethylamino-thiophen-2-ylmethylene)-amino]-thiophene-3,4-dicarboxylic acid diethyl ester (56 mg) and refluxed for seven hours. The reaction affords a purple-grey powder (53 mg, 72%) after purification by flash chromatography. 1H-NMR (300 MHz, [D] acetone): δ=8.55 (s, 1H), 8.36 (s, 1H), 8.06 (d, 1H, 3J=4.3 Hz), 7.66 (d, 1H, 3J=4.4 Hz), 7.55 (d, 1H, 3J=4.6 Hz), 6.19 (d, 1H, 3J=4.6 Hz), 4.36 (q, 2H, 3J=7.3 Hz), 4.25 (q, 2H, 3J=7.1 Hz), 3.55 (q, 4H, 3J=7.5 Hz), 1.39 (t, 3H, 3J=7.1 Hz), 1.34 (t, 3H, 3J=7.2 Hz), 1.28 (t, 6H, 3J=7.1 Hz). 13C-NMR (300 MHz, [D] acetone): δ=173.0, 167.5, 164.1, 162.9, 149.7, 143.7, 132.9, 131.6, 131.3, 130.2, 130.1, 129.7, 129.1, 127.6, 114.0, 104.9, 61.4, 60.2, 39.2, 14.2, 13.8, 10.8. +TOF-MS: m/z 563.10838. Calculated for C24H26O6N4S3 563.10872.
Sources & evidence
- ORD record
- ord-1195621b231b40b0976159e1fa04f7a5
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08034895B2
Reaction notes
Loading…