Diisopropylethylamine → HCID 86626082, compound

HRID 390615Notes

Reaction equation

HRID 390615 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].C(N(C(C)C)CC)(C)C.[CH3:23][O:24]/[C:25](=[CH:30]\[C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([NH:43][CH3:44])[CH:38]=2)=[CH:33][CH:32]=1)/[C:26]([O:28][CH3:29])=[O:27]>>[CH3:23][O:24]/[C:25](=[CH:30]\[C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([N:43]([CH3:44])[C:2]([O:4][C:5]3[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=3)=[O:3])[CH:38]=2)=[CH:33][CH:32]=1)/[C:26]([O:28][CH3:29])=[O:27]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 86626083HCID 86626083, compound

Product 1

HCID 86626082HCID 86626082, compoundYield 100%

Procedure

3.9 g (19.4 mmol) of 4-nitrophenyl chloroformate and then 3.4 mL (19.4 mmol) of diisopropylethylamine are added to a solution of 4.8 g (16.1 mmol) of methyl (Z)-2-methoxy-3-(3′-methylaminobiphenyl-4-yl)acrylate. The reaction medium is stirred at room temperature for 2 hours. The reaction medium is hydrolyzed and then extracted with dichloromethane. The organic phase is washed with water, dried over magnesium sulfate, filtered and evaporated. 7.4 g (100%) of methyl (Z)-2-methoxy-3-{3′-[methyl-(4-nitrophenoxycarbonyl)amino]biphenyl-4-yl}acrylate are obtained in the form of a tacky foam.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic phase is washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3d0ff121b78e4b3aaf9419e9fc0ed3d3
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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