2-Acetylthiophene → (2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-thiophen-2-yl-methanone

HRID 2086920

反応式

HRID 2086920 の反応式
[C:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)(=O)C.[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]([CH2:16][C:17]#[N:18])=[O:15].C1(=O)CCCC1.N1CCOCC1.[S]>>[NH2:18][C:17]1[S:5][C:6]2[CH2:1][CH2:4][CH2:8][C:7]=2[C:16]=1[C:14]([C:10]1[S:9][CH:13]=[CH:12][CH:11]=1)=[O:15]

参加物

6

反応物 5

HCID 69202-AcetylthiopheneHCID 8083MorpholineHCID 8452CyclopentanoneHCID 1418532-Thenoylacetonitrile2 回HCID 5362487Sulfur

生成物 1

HCID 9899694(2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-thiophen-2-yl-methanone収率 67%

実験手順

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). Cyclopentanone (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: 67%; IR (KBr) cm−1: 3344, 3242, 3130, 1566, 1435, 1264, 1031, 771, 747; 1H NMR (CDCl3):δ2.27 (m, 2H), 2.47 (t, 2H, J=7.4 Hz), 2.70 (t, 2H, J=7 Hz), 6.65 (bs, 2H), 7.06 (dd, 1H, J=3.8 and 4.8 Hz), 7.37 (dd,1H, J=1.0 and 4.6 Hz), 7.53 (dd, 1H, J=5.0 and 1.2 Hz); yellow solid, mp: 133-134° C. (petroleum ether).

出典と根拠

ORDレコード
ord-3c89dfbf855441708a96ccaae34f89ca
出典データセット
uspto-grants-2004_04
特許番号
US06727258B2

関連ノート

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