3-Butenoic acid → Methyl 3-[2-(3-butenoylamino)ethyl]-1-benzofuran-5-carboxylate

HRID 395576Notes

Reaction equation

HRID 395576 reaction equation
[CH:1]([CH2:3][C:4](O)=[O:5])=[CH2:2].OC1C2N=NNC=2C=CC=1.Cl.[NH2:18][CH2:19][CH2:20][C:21]1[C:25]2[CH:26]=[C:27]([C:30]([O:32][CH3:33])=[O:31])[CH:28]=[CH:29][C:24]=2[O:23][CH:22]=1>ClCCl>[C:4]([NH:18][CH2:19][CH2:20][C:21]1[C:25]2[CH:26]=[C:27]([C:30]([O:32][CH3:33])=[O:31])[CH:28]=[CH:29][C:24]=2[O:23][CH:22]=1)(=[O:5])[CH2:3][CH:1]=[CH2:2]

Participants

5

Reactant 3

HCID 327433-Butenoic acidHCID 18175082Methyl 3-(2-aminoethyl)-1-benzofuran-5-carboxylate hydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 9882372Methyl 3-[2-(3-butenoylamino)ethyl]-1-benzofuran-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

Vinylacetic acid (1 mmol), 1-ethyl-3-(3-dimethylaminopropyl-3-ethyl)carbodiimide hydrochloride (E.D.C.) (1.1 mmol) and hydroxybenzotriazole (HOBT) (1.1 mmol) are dissolved in dichloromethane (30 ml) in a flask cooled to −20° C. After 30 minutes, the compound obtained in Step A of Example 63 (1 mmol), dissolved in dichloromethane (20 ml), is added dropwise. The reaction mixture is stirred for 30 minutes at −20° C. and then overnight at ambient temperature. The dichloromethane is evaporated off and the residue is purified by chromatography on a silica gel column.

Workup

  1. additionis added dropwise
  2. customovernight
  3. customat ambient temperature
  4. customThe dichloromethane is evaporated off
  5. customthe residue is purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-272fcb8de04b4f159e029e3cc931618e
Source dataset
uspto-grants-2003_08
Patent number
US06605632B1

Reaction notes

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