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

HRID 2098155

Reaction equation

HRID 2098155 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-8e82bdd650154a31b565d65e00c8be17
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Linked notes

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