N-(2-aminoethyl)acetamide → N-{2-[(5-bromofuran-2-yl)formamido]ethyl}acetamide

HRID 34946

Reaction equation

HRID 34946 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7](Cl)=[O:8])=[CH:4][CH:3]=1.[C:10]([NH:13][CH2:14][CH2:15][NH2:16])(=[O:12])[CH3:11]>C(Cl)Cl.C(N(CC)CC)C>[NH:13]([CH2:14][CH2:15][NH:16][C:7]([C:5]1[O:6][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:8])[C:10]([CH3:11])=[O:12]

Participants

5

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 27570115-Bromofuran-2-carbonyl chloride

Product 1

HCID 13800218N-{2-[(5-bromofuran-2-yl)formamido]ethyl}acetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 22.6 g of 5-bromo-2-furancarboxylic acid chloride in 100 ml of methylene chloride was added dropwise within 20 minutes at 0°-8° to a solution, pre-cooled to 0°, of 11.0 g of monoacetyl-ethylenediamine in 250 ml of methylene chloride and 18 ml of triethylamine. The reaction mixture was stirred at room temperature overnight, suction filtered and washed with methylene chloride. There was obtained N-(2-acetamino ethyl)-5-bromo-2-furancarboxamide as pale beige crystals, m.p. 175°-176°.

Workup

  1. filtrationsuction filtered
  2. washwashed with methylene chloride

Sources & evidence

ORD record
ord-06adfa65536a4672ba2c77c29a74e2ea
Source dataset
uspto-grants-1988_08
Patent number
US04764522

Linked notes

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