Morpholine → HCID 9921248, compound
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.C1(=O)CCCC1.N1CCOCC1.[S]>>[NH2:18][C:17]1[S:6][C:7]2[CH2:2][CH2:1][CH2:4][C:8]=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). Cyclopentanone (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: 71%; IR (KBr) cm−1: 3330, 3117, 2846, 1569, 1448, 1435, 1265, 855, 836, 757, 715; 1H NMR (CDCl3):δ2.24 (m, 4H), 2.71 (m, 2H), 6.83 (bs, 2H), 7.33 (m, 2H), 7.56 (m, 1H); yellow solid, mp: 125-127° C. (petroleum ether).
Sources & evidence
- ORD record
- ord-90e01c4312cd48f3b503e7ec89c27de9
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06727258B2
Reaction notes
Loading…