Triethylamine → HCID 692365, compound

HRID 279198

Reaction equation

HRID 279198 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)/[CH:7]=[CH:8]/[C:9]([OH:11])=O)([O-:3])=[O:2].[C:15]([O:24][CH3:25])(=[O:23])[C:16]1[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=1)[NH2:18].C(N(CC)CC)C>S(Cl)(Cl)=O.CN(C)C=O.O1CCOCC1>[CH3:25][O:24][C:15]([C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH:18][C:9](=[O:11])/[CH:8]=[CH:7]/[C:6]1[CH:12]=[CH:13][CH:14]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:23]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 6871263-Nitrocinnamic acid

Product 1

HCID 692365HCID 692365, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 24386Thionyl ChlorideSolventHCID 312751,4-DioxaneSolvent

Procedure

965 mg (5.0 mmol) of trans-3-nitrocinnamic acid are refluxed for 20 minutes in 3 ml of thionyl chloride after the addition of one drop of dimethylformamide. Then the mixture is evaporated to dryness in vacuo and the resulting acid chloride is dissolved in 10 ml of dioxane. This solution is slowly added dropwise, with stirring, at ambient temperature, to a solution of 756 mg (5.0 mmol) of methyl anthranilate and 1.5 ml of triethylamine in 10 ml of dioxane. After one hour the solvent is evaporated off in vacuo, the residue is stirred into about 10 ml of water, then filtered off and the resulting crude product is purified by column chromatography over silica gel (eluant: dichloromethane/petroleum ether=2:1).

Workup

  1. customThen the mixture is evaporated to dryness in vacuo
  2. dissolutionthe resulting acid chloride is dissolved in 10 ml of dioxane
  3. additionThis solution is slowly added dropwise
  4. customAfter one hour the solvent is evaporated off in vacuo
  5. filtrationfiltered off
  6. customthe resulting crude product is purified by column chromatography over silica gel (eluant: dichloromethane/petroleum ether=2:1)

Sources & evidence

ORD record
ord-45a77e7e73d34144af64f251bb19d2a5
Source dataset
uspto-grants-2002_03
Patent number
US06362210B1

Linked notes

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