Cyclohexanone → (2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-thiophen-3-yl-methanone
Reaction equation
[C:1]([C:4]1[CH:8]=[CH:7][S:6]C=1)(=O)[CH3:2].[S:9]1[CH:13]=[CH:12][C:11]([C:14]([CH2:16][C:17]#[N:18])=[O:15])=[CH:10]1.[C:19]1(=O)CCCCC1.N1CCOCC1.[S]>>[NH2:18][C:17]1[S:6][C:7]2[CH2:8][CH2:4][CH2:1][CH2:2][C:19]=2[C:16]=1[C:14]([C:11]1[CH:12]=[CH:13][S:9][CH:10]=1)=[O:15]Participants
6
Procedure
The procedure of Example 1 was followed except that 3-acetylthiophene (Aldrich) was used in place of acetophenone to prepare the corresponding 2-(thiophene-3-carbonyl)acetonitrile (Steps A and B). Cyclohexanone (Aldrich), 2-(thiophene-3-carbonyl)acetonitrile, morpholine, and sulfur were reacted according to the procedure of Step C, Example 1, to afford the desired compound. Yield: 67%; IR (KBr) cm−1: 3323, 3107, 2929, 1576, 1433, 1266, 1151, 1080, 825, 726; 1H NMR (CDCl3):δ1.55 (m, 2H), 1.77 (m, 2H), 2.01 (t, 2H, J=6 Hz), 2.54 (t, 2H, J=6.2 Hz), 6.46 (bs, 2H), 7.28 (m, 2H), 7.58 (t, 1H, J=2.2 Hz); yellow solid, mp: 133-135° C. (petroleum ether).
Sources & evidence
- ORD record
- ord-96b0f02c99c848b19c75ecb9deb50e4b
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06727258B2
Reaction notes
Loading…