Triethylamine → 7-(2,6-Dichlorobenzoylamino)-2-ethyl-3-methylbenzo[b]furan

HRID 342446Notes

Reaction equation

HRID 342446 reaction equation
[NH2:1][C:2]1[C:7]2[O:8][C:9]([CH2:12][CH3:13])=[C:10]([CH3:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:16]=1[C:17](Cl)=[O:18].C(N(CC)CC)C>ClCCCl.ClCCl>[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:16]=1[C:17]([NH:1][C:2]1[C:7]2[O:8][C:9]([CH2:12][CH3:13])=[C:10]([CH3:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 783922,6-Dichlorobenzoyl chlorideHCID 25219482(2-Ethyl-3-methyl-1-benzofuran-7-yl)amine

Product 1

HCID 702004567-(2,6-Dichlorobenzoylamino)-2-ethyl-3-methylbenzo[b]furanYield 35.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 7-amino-2-ethyl-3-methylbenzo[b]furan (858 mg), 2,6-dichlorobenzoyl chloride (1.23 g) and triethylamine (1.23 g) in 1,2-dichloroethane (17 ml) was stirred for 3 hours at 70° C. The mixture was diluted with dichloromethane, washed with diluted hydrochloric acid and brine, dried over sodium sulfate, and evaporated in vacuo to give a solid. The residue solid was crystallized from a mixture of ethanol (20 ml) and water (2 ml) to give 7-(2,6-dichlorobenzoylamino)-2-ethyl-3-methylbenzo[b]furan (610 mg).

Workup

  1. washwashed with diluted hydrochloric acid and brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo
  4. customto give a solid
  5. customThe residue solid was crystallized from a mixture of ethanol (20 ml) and water (2 ml)

Sources & evidence

ORD record
ord-12eacca4b6f04923b597a8719f1b3091
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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