1,1'-Carbonyldiimidazole → 2-(3,4,5-trimethoxyphenyl)-2-acetoxy-N-methyl-N-[1-(3-methoxyphenyl)ethyl]acetamide

HRID 1666314Notes

Reaction equation

HRID 1666314 reaction equation
[C:1]([O:4][CH:5]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=1)[C:6]([OH:8])=O)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:33][O:34][C:35]1[CH:36]=[C:37]([CH:41]([NH:43][CH3:44])[CH3:42])[CH:38]=[CH:39][CH:40]=1>ClCCl>[CH3:20][O:19][C:11]1[CH:10]=[C:9]([CH:5]([O:4][C:1](=[O:3])[CH3:2])[C:6]([N:43]([CH3:44])[CH:41]([C:37]2[CH:38]=[CH:39][CH:40]=[C:35]([O:34][CH3:33])[CH:36]=2)[CH3:42])=[O:8])[CH:14]=[C:13]([O:15][CH3:16])[C:12]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 148716881-(3-Methoxyphenyl)-N-methylethanamineHCID 67081678alpha-Acetoxy-3,4,5-trimethoxyphenyl-acetic acid

Product 1

HCID 670818362-(3,4,5-trimethoxyphenyl)-2-acetoxy-N-methyl-N-[1-(3-methoxyphenyl)ethyl]acetamideYield 67.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of α-acetoxy-3,4,5-trimethoxyphenyl-acetic acid (7.1 g) in dichloromethane (50 ml) was reacted with 1,1′-carbonyldiimidazole (4.06 g) at room temperature for 30 minutes. The solution was refluxed for 30 minutes, after which 1-(3-methoxyphenyl)-N-methylethylamine (4.13 g) dissolved in dichloromethane (10 ml) was added. The mixture was stirred at room temperature for 2 hours, after which it was washed with aqueous hydrochloric acid (20 ml, 1M) followed by aqueous sodium hydrogen carbonate (20 ml, 0.5 M). The organic phase was dried and concentrated to dryness, leaving crude 2-(3,4,5-trimethoxyphenyl)-2-acetoxy-N-methyl-N-[1-(3-methoxyphenyl)ethyl]acetamide (7.27 g).

Workup

  1. temperatureThe solution was refluxed for 30 minutes
  2. additionwas added
  3. washafter which it was washed with aqueous hydrochloric acid (20 ml, 1M)
  4. customThe organic phase was dried
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f32053fd8ae94d6d818fe6f4e0d4de44
Source dataset
uspto-grants-2011_10
Patent number
US08044067B2

Reaction notes

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