Veratric Acid → 3-(3,4-Dimethoxybenzoyl)amino-epsilon-caprolactam

HRID 1463464Notes

Reaction equation

HRID 1463464 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.[NH2:14][CH:15]1[CH2:22][CH2:21][CH2:20][NH:19][C:17](=[O:18])[CH2:16]1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([NH:14][CH:15]1[CH2:22][CH2:21][CH2:20][NH:19][C:17](=[O:18])[CH2:16]1)=[O:8]

Participants

4

Reactant 2

HCID 7121Veratric AcidHCID 215841384-Aminoazepan-2-one

Product 1

HCID 190904203-(3,4-Dimethoxybenzoyl)amino-epsilon-caprolactamYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N'-Carbonyldiimidazole (9.79 g) was added to a solution of 3,4-dimethoxybenzoic acid (10.0 g) in THF (300 ml) and the whole was stirred for 30 mins. at room temperature. Then, following by addition of 3-amino-ε-caprolactam (7.04 g), the mixture was stirred for 5 hrs. The resultant precipitate was collected by filtration, washed and dried under reduced pressure to give the title compound (8.5 g). This product was used in the following reaction without purification. m.p. 190°-191°.

Workup

  1. customat room temperature
  2. stirringthe mixture was stirred for 5 hrs
  3. filtrationThe resultant precipitate was collected by filtration
  4. washwashed
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-79075dfc97a544e6b01afa8b44a913e5
Source dataset
uspto-grants-1994_04
Patent number
US05300639

Reaction notes

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