2-Methoxyphenylacetic acid → HCID 6464944, compound

HRID 1029962Notes

Reaction equation

HRID 1029962 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=O.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][NH2:19]>ClCCl>[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][NH:19][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 71342-Methoxyphenylacetic acidHCID 34005(2-Thienylmethyl)amine

Product 1

HCID 6464944HCID 6464944, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N'-Carbonyldiimidazole (8.1 g) is added to a stirred solution of 2-(2-methoxyphenyl)acetic acid (8.3 g) in anhydrous dichloromethane (80 cc), cooled to +5° C.; stirring of the reaction mixture is continued for 1 hour and a half and (2-thienyl)methylamine (5.1 cc) is then added. Stirring of the reaction mixture is continued for 1 hour at +5° C. and then for 2 hours at ambient temperature. The reaction mixture is then washed with distilled water (2×40 cc); the organic solution is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The solid residue obtained is washed with isopropyl ether (30 cc), drained and dried. N-(2-Thienyl)methyl-2-(2-methoxyphenyl)acetamide (10.5 g) melting at 84° C. is obtained.

Workup

  1. temperaturecooled to +5° C.
  2. stirringStirring of the reaction mixture
  3. waitis continued for 1 hour at +5° C.
  4. waitfor 2 hours at ambient temperature
  5. washThe reaction mixture is then washed with distilled water (2×40 cc)
  6. dry with materialthe organic solution is dried over magnesium sulphate
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  8. customThe solid residue obtained
  9. washis washed with isopropyl ether (30 cc)
  10. customdried

Sources & evidence

ORD record
ord-ef14f16442cb4d548e7377ff5aadc931
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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