Triethylamine → HCID 19177455, compound

HRID 1176538Notes

Reaction equation

HRID 1176538 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4](Cl)=[O:5].[NH2:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][C:2]([CH3:7])=[CH:3][C:4]([NH:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 1023943-Methyl-2-butenoyl chloride

Product 1

HCID 19177455HCID 19177455, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A solution of 12.5 ml of 3-methylbut-2-enoyl chloride in 110 ml of toluene is added dropwise at room temperature to a solution of 13.4 ml of methyl 2-aminobenzoate and 21.8 ml of triethylamine in 110 ml of toluene. After 30 minutes, the reaction mixture is diluted with toluene, washed with 1N HCl (2×), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a white solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.34 (1:10 EtOAc-heptane); Rt=4.78.

Workup

  1. washwashed with 1N HCl (2×)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-178a8e71d32745ae943d09b04c581477
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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