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

HRID 892619Notes

Reaction equation

HRID 892619 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 o 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 used in the following reaction without purification. m.p. 190°-191°.

Workup

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

Sources & evidence

ORD record
ord-d504832d8abb4889ba08917ca0361b24
Source dataset
uspto-grants-1992_06
Patent number
US05118806

Reaction notes

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