Dichloromethane → N-[3-[(Z)-N'-hydroxycarbamimidoyl]thiophen-2-yl]-2-(4-methoxyphenyl)acetamide

HRID 2098155

反応式

HRID 2098155 の反応式
[C:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[NH:8][C:9](=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)#[N:2].C(Cl)Cl.C(N(CC)CC)C.Cl.[NH2:31][OH:32]>C(O)C.C(=O)(O)[O-].[Na+]>[OH:32][NH:31][C:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[NH:8][C:9](=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=[NH:2]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 2404093N-(3-cyanothiophen-2-yl)-2-(4-methoxyphenyl)acetamide

生成物 1

HCID 178490500N-[3-[(Z)-N'-hydroxycarbamimidoyl]thiophen-2-yl]-2-(4-methoxyphenyl)acetamide

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of N-(3-cyanothiophen-2-yl)-2-(4-methoxyphenyl)acetamide (234 mg, 0.859 mmol) in a mixture of ethanol (5 mL), methylene chloride (0.5 mL) and triethylamine (202 4, 1.46 mmol) was added hydroxylamine hydrochloride (90 mg, 1.29 mmol). The resulting solution was stirred at room temperature for 18 h and was subsequently diluted with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic phases were combined, dried (Na2SO4), filtered, concentrated under vacuum and purified on a silica gel column (eluant hexane/ethyl acetate, 7/3 to 2/8) to give N-(3-(N-hydroxycarbamimidoyl)thiophen-2-yl)-2-(4-methoxyphenyl)acetamide. Retention time (min)=1.161, method [1], MS (ESI) 306.1 (M+H).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. custompurified on a silica gel column (eluant hexane/ethyl acetate, 7/3 to 2/8)

出典と根拠

ORDレコード
ord-8e82bdd650154a31b565d65e00c8be17
出典データセット
uspto-grants-2013_05
特許番号
US08450363B2

関連ノート

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