Ammonia → 4-Benzofuranacetamide

HRID 751491Notes

Reaction equation

HRID 751491 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[O:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[C:21]([CH2:22][C:23]([OH:25])=O)[C:16]=2[CH:15]=[CH:14]1.N>O1CCCC1>[O:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[C:21]([CH2:22][C:23]([NH2:3])=[O:25])[C:16]=2[CH:15]=[CH:14]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 2767551113405-11-1

Product 1

HCID 179764934-BenzofuranacetamideYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

Add 1,1′-carbonyldiimidazole (2.3 g, 14.2 mmol) to a solution of benzofur-4-ylacetic acid (2.5 g, 14.2 mmol) in anhydrous tetrahydrofuran (12 mL) under nitrogen and stir at 20° C. for 4 hours. Bubble anhydrous ammonia through the solution, dilute with anhydrous tetrahydrofuran (10 mL), and stir at 20° C. for 18 hours. Concentrate under reduced pressure, and wash the solid with aqueous sodium hydrogen sulfate and distilled water. Dry under vacuum to obtain 2.3 g (93%) of the title compound as a pale yellow solid. Mass spectrum (ES, m/z) (M+H)=176.1.

Workup

  1. stirringstir at 20° C. for 18 hours
  2. concentrationConcentrate under reduced pressure
  3. washwash the solid with aqueous sodium hydrogen sulfate
  4. distillationdistilled water
  5. customDry under vacuum

Sources & evidence

ORD record
ord-7056da19d96a4a7caac1121624ce544c
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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