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

HRID 2098155

반응식

HRID 2098155 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 516892Sodium Bicarbonate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-8e82bdd650154a31b565d65e00c8be17
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450363B2

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