Dichloromethane → N-(3-(N-hydroxycarbamimidoyl)thiophen-2-yl)-2-(4-methoxyphenyl)acetamide

HRID 1519941

反応式

HRID 1519941 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][N: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)[NH2:2]

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 136414311N-(3-(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 μL, 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-9a58c8edd7d643c793c36081ad1373fd
出典データセット
uspto-grants-2015_07
特許番号
US09073891B2

関連ノート

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