Water → N-[(Thiophen-2-yl)methyl]ethanimidic acid

HRID 1484887Notes

Reaction equation

HRID 1484887 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH2:7].[C:8](OC(=O)C)(=[O:10])[CH3:9].O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8](=[O:10])[CH3:9]

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 34005(2-Thienylmethyl)amine

Product 1

HCID 30617N-[(Thiophen-2-yl)methyl]ethanimidic acidYield 91%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of thiophen-2-ylmethanamine (600 mg, 5.30 mmol), DMAP (130 mg, 1.06 mmol, 0.2 equiv) and acetic anhydride (648 mg, 6.36 mmol, 1.2 equiv) in DCM (20 mL) was stirred at room temperature for 2 h. Water was added and the reaction was extracted with EA. The combined organic layers were dried (Na2SO4), filtered. The filtrate was concentrated to afford the compound N-(thiophen-2-ylmethyl)acetamide (745 mg, 91%). LC-MS (m/z)=156 [M+H]+.

Workup

  1. extractionthe reaction was extracted with EA
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-eeae402f90424c95bd8e04d2099787ba
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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