Isopropylamine → HCID 18963781, compound

HRID 2226883Notes

Reaction equation

HRID 2226883 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:14]([OH:16])=O)[CH3:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:29]([NH2:32])([CH3:31])[CH3:30]>O1CCCC1.C(OCC)(=O)C>[CH3:3][CH:2]([O:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:14]([NH:32][CH:29]([CH3:31])[CH3:30])=[O:16])[CH3:1]

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 10704137HCID 10704137, compound

Product 1

HCID 18963781HCID 18963781, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(1-methylethoxy)-2-benzofurancarboxylic acid (250 mg, 1.14 mmol) and 1,1'-carbonyldiimidazole (240 mg, 1.48 mmol) in 7 mL of tetrahydrofuran is heated at reflux for 1 hour. The reaction solution is cooled to room temperature and i-propylamine (0.58 mL, 6.84 mmol) is added and the reaction mixture is stirred at room temperature for 30 minutes. The reaction is diluted with ethyl acetate and washed with brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography eluting with ethyl acetate:hexane (1:2 to 1:1) provides 3-(1-methylethoxy)-N-(1-methylethyl)-2-benzofurancarboxamide in 72% yield as a yellow oil.

Workup

  1. temperatureat reflux for 1 hour
  2. washwashed with brine
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washChromatography eluting with ethyl acetate:hexane (1:2 to 1:1)

Sources & evidence

ORD record
ord-a68d5d15fd52467abee0e1387e3d0382
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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