Morpholine → (2-Amino-4,5-dimethylthiophen-3-yl)-(5-bromothiophen-2-yl)-methanone

HRID 2086925Notes

Reaction equation

HRID 2086925 reaction equation
[C:1]([C:4]1[S:5]C(Br)=C[CH:8]=1)(=O)[CH3:2].[Br: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]([Br:10])=[CH:12][CH:13]=1)=[O:17]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 793352-Acetyl-5-bromothiopheneHCID 5362487SulfurHCID 112876633-(5-Bromothiophen-2-yl)-3-oxopropanenitrile2×

Product 1

HCID 9836568(2-Amino-4,5-dimethylthiophen-3-yl)-(5-bromothiophen-2-yl)-methanoneYield 51%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The procedure of Example 1 was followed except that 2-acetyl-5-bromothiophene (Aldrich) was used in place of acetophenone to prepare the corresponding 2-(5-bromothiophene-2-carbonyl)acetonitrile (Steps A and B). 2-Butanone (Aldrich), 2-(5-bromothiophene-2-carbonyl)acetonitrile, morpholine, and sulfur were reacted according to the procedure of Step C, Example 1, to afford the desired compound. Yield: 51%; IR (KBr) cm−1: 3348, 1559, 1448, 1413, 1388, 1318, 1263, 974, 769; 1H NMR (CDCl3):δ2.16 (s, 6H), 5.90 (bs, 2H), 7.02 (d, J=4 Hz, 1H), 7.11 (d, 1H, J=4 Hz); orange solid, mp: 128-130° C. (petroleum ether).

Sources & evidence

ORD record
ord-6908ad2b1da8429e80002b9b42d4ce56
Source dataset
uspto-grants-2004_04
Patent number
US06727258B2

Reaction notes

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