N,N-Diethylethylenediamine → HCID 19804340, compound

HRID 893722Notes

Reaction equation

HRID 893722 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([Cl:13])=[O:12])[C:5]2[O:6][CH:7]=[CH:8][C:4]=2[CH:3]=1.[CH2:14]([N:16]([CH2:20][CH3:21])[CH2:17][CH2:18][NH2:19])[CH3:15]>C(Cl)Cl>[ClH:13].[Br:1][C:2]1[CH:10]=[C:9]([C:11]([NH:19][CH2:18][CH2:17][N:16]([CH2:20][CH3:21])[CH2:14][CH3:15])=[O:12])[C:5]2[O:6][CH:7]=[CH:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 53760789HCID 53760789, compound

Product 1

HCID 19804340HCID 19804340, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of 5-bromobenzo[b]furan-7-carboxylic acid chloride (1.5 g, 5.8 mmol) in 15 ml of CH2Cl2, there was added N,N-diethylethylenediamine (0.74 g, 6.4 mmol) in 10 ml of CH2Cl2. After stirring at ambient temperature overnight, the precipitate was collected on a filter to give the crude amide (1.14 g, 53.2%). This was recrystallized from ethanol (decolorization with charcoal) to give 0.54 g (24.8%) of the desired amide as a white solid, mp 202°-203.5° C. IR (KBr) 1675 (C=0) cm-1.

Workup

  1. customthe precipitate was collected on
  2. filtrationa filter
  3. customto give the crude amide (1.14 g, 53.2%)
  4. customThis was recrystallized from ethanol (decolorization with charcoal)

Sources & evidence

ORD record
ord-b4cfdbf6c44b44a19570c37e11ce6f37
Source dataset
uspto-grants-1992_06
Patent number
US05126364

Reaction notes

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