Morpholine → HCID 9856737, compound

HRID 2086928Notes

Reaction equation

HRID 2086928 reaction equation
[C:1]([C:4]1[S:5]C(Cl)=C[CH:8]=1)(=O)[CH3:2].[Cl:10][C:11]1[S:15][C:14]([C:16]([CH2:18][C:19]#[N:20])=[O:17])=[CH:13][CH:12]=1.N1CCOCC1.[S]>CC(=O)CC>[NH2:20][C:19]1[S:5][C:4]([CH3:8])=[C:1]([CH3:2])[C:18]=1[C:16]([C:14]1[S:15][C:11]([Cl:10])=[CH:12][CH:13]=1)=[O:17]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 805722-Acetyl-5-chlorothiopheneHCID 5362487SulfurHCID 125401813-(5-Chlorothiophen-2-yl)-3-oxopropanenitrile2×

Product 1

HCID 9856737HCID 9856737, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The procedure of Example 1 was followed except that 2-acetyl-5-chlorothiophene (Aldrich) was used in place of acetophenone to prepare the corresponding 2-(5-chlorothiophene-2-carbonyl)acetonitrile (Steps A and B). 2-Butanone (Aldrich), 2-(5-chlorothiophene-2-carbonyl)acetonitrile, morpholine, and sulfur were reacted according to the procedure of Step C, Example 1, to afford the desired compound. Yield: 46%; IR (KBr) cm−1: 3377, 3259, 2918, 1551, 1424, 1326, 1266, 1003, 764; 1H NMR (CDCl3):δ1.90 (s, 3H), 2.17 (s, 3H), 5.77 (bs, 2H), 6.89 (d, 1H, J=4 Hz), 7.16 (d, 1H, J=4 Hz); red solid, mp: 125-127° C. (petroleum ether).

Sources & evidence

ORD record
ord-47032fe487e5489e98cb171265aacf87
Source dataset
uspto-grants-2004_04
Patent number
US06727258B2

Reaction notes

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