2-Acetylthiophene → HCID 700447, compound

HRID 2216902Notes

Reaction equation

HRID 2216902 reaction equation
[C:1]([C:4]1[S:5]C=C[CH:8]=1)(=O)[CH3:2].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]([CH2:16][C:17]#[N:18])=[O:15].N1CCOCC1.[S]>CC(=O)CC>[NH2:18][C:17]1[S:5][C:4]([CH3:8])=[C:1]([CH3:2])[C:16]=1[C:14]([C:10]1[S:9][CH:13]=[CH:12][CH:11]=1)=[O:15]

Participants

6

Reactant 4

HCID 69202-AcetylthiopheneHCID 8083MorpholineHCID 1418532-Thenoylacetonitrile2×HCID 5362487Sulfur

Product 1

HCID 700447HCID 700447, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

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-Butanone (Aldrich), 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: 44%; IR (KBr) cm−1: 3390, 3269, 1552, 1429, 1272, 852, 772; 1H NMR (CDCl3):δ 1.86 (s, 3H), 2.17 (s, 3H), 5.78(bs, 2H), 7.07 (dd, 1H, J=3.8 and 4.8 Hz), 7.56 (dd, 1H, J=2.8 and 0.8 Hz), 7.58 (dd, 1H, J=5.0 and 0.8 Hz); orange solid, mp: 117–118° C. (petroleum ether).

Sources & evidence

ORD record
ord-a60c16f910bb4322b5d5f89c00adc0f2
Source dataset
uspto-grants-2006_09
Patent number
US07112607B2

Reaction notes

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