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3-Chlorobenzo(b)thiophene-2-carbonyl chloride → (2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-(3-chloro-1-benzothien-2-yl)ethanone

HRID 448031
ノート
印刷プレビュー

反応式

HRID 448031 の反応式
[I-].[CH2:2]([N+:6]1[C:10]([CH3:11])=[CH:9][S:8][C:7]=1[CH3:12])[CH2:3][CH2:4][CH3:5].[Cl:13][C:14]1[C:15]2[CH:25]=[CH:24][CH:23]=[CH:22][C:16]=2[S:17][C:18]=1[C:19](Cl)=[O:20]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CS(C)=O.CO>[CH2:2]([N:6]1[C:10]([CH3:11])=[CH:9][S:8]/[C:7]/1=[CH:12]\[C:19]([C:18]1[S:17][C:16]2[CH:22]=[CH:23][CH:24]=[CH:25][C:15]=2[C:14]=1[Cl:13])=[O:20])[CH2:3][CH2:4][CH3:5]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 5198983-Chlorobenzo(b)thiophene-2-carbonyl chlorideHCID 691651093-Butyl-2,4-dimethylthiazol-3-ium iodide

生成物 1

HCID 24955694(2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-(3-chloro-1-benzothien-2-yl)ethanone

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒3 回
HCID 22036561
Dimethyl sulfoxide methanol
溶媒

実験手順

In a 20 mL vial a solution of 3-butyl-2,4-dimethylthiazol-3-ium iodide (47.92 mg, 0.16 mmol) dissolved in CH2Cl2 (0.5 mL) was added, followed by the addition of DMAP (49.24 mg, 0.40 mmol) dissolved in CH2Cl2 (0.8 mL). Then, to the solution was added 3-chlorobenzo[b]thiophene-2-carbonyl chloride (37.0 mg, 0.16 mmol) dissolved in CH2Cl2 (0.5 mL). The vial was capped and shaken overnight at room temperature. The residue was dissolved in 1:1 DMSO/MeOH and purified by reverse phase HPLC using a method analogous to that described in Example 53 to provide the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 0.98 (t, 3 H) 1.39-1.48 (m, 2 H) 1.70-1.80 (m, 2 H) 2.31-2.37 (m, 3 H) 4.00-4.09 (m, 2 H) 6.67-6.70 (m, 1 H) 6.85-6.89 (m, 1 H) 7.49-7.56 (m, 2 H) 7.85-7.92 (m, 1 H) 8.01-8.07 (m, 1 H); MS (ESI) positive ion 364 (M+H).

後処理

  1. additionwas added
  2. customThe vial was capped
  3. custompurified by reverse phase HPLC

出典と根拠

ORDレコード
ord-9aab53e04772489a9a2a634b52bb715e
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08481574B2

反応ノート

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