Cyclohexanone → (2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(5-bromothiophen-2-yl)-methanone

HRID 2216904Notes

Reaction equation

HRID 2216904 reaction equation
[C:1]([C:4]1[S:5][C:6](Br)=[CH:7][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.C1(=O)CCCCC1.N1CCOCC1.[S]>>[NH2:20][C:19]1[S:5][C:6]2[CH2:2][CH2:1][CH2:4][CH2:8][C:7]=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 5

HCID 7967CyclohexanoneHCID 8083MorpholineHCID 793352-Acetyl-5-bromothiopheneHCID 5362487SulfurHCID 112876633-(5-Bromothiophen-2-yl)-3-oxopropanenitrile2×

Product 1

HCID 10268919(2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(5-bromothiophen-2-yl)-methanoneYield 66%

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). Cyclohexanone (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: 66%; IR (KBr) cm−1: 3379, 3247, 2918, 1577, 1548, 1432, 1416, 1273, 761; 1H NMR (CDCl3):δ 1.63 (m, 2H), 1.79 (m, 2H), 2.24 (t, 2H, J=5.8 Hz), 2.55 (t, 2H, J=5.8 Hz), 6.11 (bs, 2H), 7.02 (d, 1H, J=4 Hz), 7.13 (d, 1H, J=4 Hz); orange solid, mp: 160–163° C. (petroleum ether).

Sources & evidence

ORD record
ord-7ea88c7378da4d7bb2ef04c4b9df90f2
Source dataset
uspto-grants-2006_09
Patent number
US07112607B2

Reaction notes

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