2-Acetylthiophene → HCID 10222972, compound
Reaction equation
C(C1[S:5]C=CC=1)(=O)C.[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]([CH2:16][C:17]#[N:18])=[O:15].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]2[S:32][CH2:31][C:30](=O)[CH2:29][S:28]2)=[CH:23][CH:22]=1.N1CCOCC1.[S]>>[NH2:18][C:17]1[S:5][C:29]2[S:28][CH:27]([C:24]3[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=3)[S:32][CH2:31][C:30]=2[C:16]=1[C:14]([C:10]1[S:9][CH:13]=[CH:12][CH:11]=1)=[O:15]Participants
Procedure
The procedure of Example 1 was followed except that 2-acetylthiophene (Aldrich) was used in place of acetophenone to prepare the corresponding 2-(thiophene-2-carbonyl)acetonitrile (Steps A and B). 2-(4-Methoxyphenyl)-1,3-dithian-5-one (Luettringhaus, Mohr, and Englehard, J. Liebig's Ann. Chem. (1963) 661: 84-94), 2-(thiophene-2-carbonyl)acetonitrile, morpholine, and sulfur were reacted according to the procedure of Step C, Example 1, to afford the desired compound. Yield: 75%; IR (KBr) cm−1: 3429, 3324, 1608, 1566, 1509, 1436, 1254, 1174, 1029, 838, 716; 1H NMR (CDCl3):δ3.69 (d, 2H, J=6.8 Hz), 3.81 (s, 3H), 3.83 (s, 1H), 6.14 (bs, 2H), 6.87 (t, 2H, J=8.8 Hz), 7.11 (m, 1H), 7.38 (d, 2H, J=8.8 Hz), 7.56 (d, 1H, J=3.2 Hz), 7.62 (d, 1H, J=5 Hz); orange solid, mp: 138-140° C. (petroleum ether).
Sources & evidence
- ORD record
- ord-16e10f7df8704d968958d610aa3cc35b
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06727258B2
Reaction notes
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