Diiodomethane → HCID 59250036、化合物

HRID 2282109ノート

反応式

HRID 2282109 の反応式
N[C:2]1[S:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[C:3]=1[C:20]#[N:21].[I:22]CI.N(OCCC(C)C)=O>C(#N)C>[C:20]([C:3]1[C:4]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[S:6][C:2]=1[I:22])#[N:21]

参加物

5

反応物 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 59250010HCID 59250010、化合物

生成物 1

HCID 59250036HCID 59250036、化合物収率 37.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
38 °C

実験手順

To a suspension of ethyl 5-amino-4-cyano-3-(2,4-dichlorophenyl)thiophene-2-carboxylate (2.92 g, 0.00856 mol) in acetonitrile (10 mL) was added diiodomethane (2.41 mL, 0.0300 mol) under an atmosphere of argon and was heated at 38° C. Isoamyl nitrite (2.61 g, 0.0214 mol) was added dropwise and the reaction mixture was cooled to room temperature and stirred for one hour. The reaction was concentrated in vacuo and column chromatography was performed to yield the title compound (1.44 g, 37%) as an orange solid. 1H NMR (400 MHz, d1-chloroform) δ: 7.53 (d, 1H, J=2.00 Hz), 7.38-7.34 (m, 1H), 7.21 (d, 1H, J=8.28 Hz), 4.25-4.15 (m, 2H), 1.21-1.16 (m, 3H).

後処理

  1. temperaturethe reaction mixture was cooled to room temperature
  2. concentrationThe reaction was concentrated in vacuo and column chromatography

出典と根拠

ORDレコード
ord-1b81e611d26d43cfa713d5bc329709d3
出典データセット
uspto-grants-2015_09
特許番号
US09139589B2

反応ノート

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