Triethylamine → Methyl 3-[2-(2-furoylamino)ethyl]-1-benzofuran-5-carboxylate

HRID 351142Notes

Reaction equation

HRID 351142 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[C:9]2[CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=[CH:13][C:8]=2[O:7][CH:6]=1.C(N(CC)CC)C.[O:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30](Cl)=[O:31]>C(Cl)Cl>[O:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30]([NH:2][CH2:3][CH2:4][C:5]1[C:9]2[CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=[CH:13][C:8]=2[O:7][CH:6]=1)=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 18175082Methyl 3-(2-aminoethyl)-1-benzofuran-5-carboxylate hydrochloride

Product 1

HCID 18174996Methyl 3-[2-(2-furoylamino)ethyl]-1-benzofuran-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 mmol of the compound obtained in Step A is introduced into 30 ml of anhydrous CH2Cl2. The temperature is lowered with the aid of an ice bath, and 1.5 mmol of triethylamine and then 1.5 mmol of 2-furoic acid chloride are added dropwise in succession. The mixture is stirred for 20 minutes, and the organic phase is then washed with water, dried over MgSO4 and evaporated. The residue is purified by chromatography on a silica gel column and the title product is recrystallised.

Workup

  1. customThe temperature is lowered with the aid of an ice bath
  2. washthe organic phase is then washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue is purified by chromatography on a silica gel column
  6. customthe title product is recrystallised

Sources & evidence

ORD record
ord-6898110ca1134045b2df01d60172494a
Source dataset
uspto-grants-2007_02
Patent number
US07183318B2

Reaction notes

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