Hydrochloric Acid → HCID 22736739, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14].[CH3:15][C:16]1[S:17][C:18]([CH3:26])=[CH:19][C:20]=1/[CH:21]=[CH:22]/[C:23]([Cl:25])=O.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.Cl>CO>[ClH:25].[CH3:15][C:16]1[S:17][C:18]([CH3:26])=[CH:19][C:20]=1/[CH:21]=[CH:22]/[C:23]1[N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]=1Participants
Procedure
To a solution of (E)-3-(2,5-dimethylthiophene-3-yl)acrylic acid (328 mg, 1.8 mmol) in benzene (10 ml) was added thionyl chloride (0.5 ml) and the mixture was heated to reflux for 60 min. Volatiles were removed by evaporation to give crude (E)-3-(2,5-dimethylthiophene-3-yl)acryloyl chloride. Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine (250 mg, 1.4 mmol) and (E)-3-(2,5-dimethylthiophene-3-yl)acryloyl chloride obtained as above according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base was dissolved with a 10% methanol solution of hydrogen chloride (5 ml). Concentration and recrystallization from ethyl acetate/ethanol yielded the titled compound. MW: 367.91; mp:>230° C.; 1H-NMR (CDCl3) δ: 8.98-8.83 (2H, m), 8.25-8.16 (1H, m), 8.10-8.02 (1H, m), 7.76-7.68 (2H, m), 7.60-7.42 (3H, m), 6.78-6.73 (1H, m), 6.61 (1H, d, J=16.1 Hz), 2.75 (3H, s), 2.38 (3H, s).
Workup
- customobtained as
- concentrationConcentration and recrystallization from ethyl acetate/ethanol
Sources & evidence
- ORD record
- ord-36d8ce68cf1c489bbea0f62345bde58e
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06713482B2
Reaction notes
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