Ammonium Hydroxide → 2-(3-Oxo-1,3-dihydro-2-benzofuran-1-yl)acetamide

HRID 1829068Notes

Reaction equation

HRID 1829068 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][C:12]([OH:14])=O)[O:3]1.[NH4+:15].[OH-]>S(Cl)(Cl)=O.C(Cl)Cl>[O:1]=[C:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[CH:4]([CH2:11][C:12]([NH2:15])=[O:14])[O:3]1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 5897301,3-Dihydro-3-oxo-1-isobenzofuranacetic acid

Product 1

HCID 43602662-(3-Oxo-1,3-dihydro-2-benzofuran-1-yl)acetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of (3-oxo-1,3-dihydro-isobenzofuran-1-yl)-acetic acid (5.0 g, 26 mmol) in thionyl chloride (10 ml) was heated at 75° C. for 15 minutes. The excess thionyl chloride was removed under vacuum to give a red oil. The red oil was dissolved in CH2Cl2 (10 ml) and then the solution was slowly added to concentrated NH4OH (40 ml) at 0° C. The resultant solid was filtered and washed with water and hexane, followed by addition of toluene. Removal of the solvent led to 2-(3-oxo-1,3-dihydro-2-benzofuran-1-yl)acetamide as a cream solid (4.2 g, 84%).

Workup

  1. customThe excess thionyl chloride was removed under vacuum
  2. customto give a red oil
  3. filtrationThe resultant solid was filtered
  4. washwashed with water and hexane
  5. additionfollowed by addition of toluene
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-3c693b07004045358802347dd17f6ea4
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

Loading…