Triethylamine → HCID 178468266, compound

HRID 128959Notes

Reaction equation

HRID 128959 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4](=[NH:8])[O:5][CH2:6][CH3:7].[CH2:13](N(CC)CC)C.[Cl:20]/[C:21](/[CH3:27])=[C:22](\C)/[C:23](Cl)=[O:24]>C1(C)C=CC=CC=1>[Cl:20][C:21]([CH3:27])=[C:22](/[N:8]=[C:4](/[O:5][CH2:6][CH3:7])\[C:3]1[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=1[Cl:1])[C:23]([CH3:13])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13029247(E)-3-chloro-2-methyl-2-butenoyl chlorideHCID 13092607Ethyl 2-chlorobenzimidate

Product 1

HCID 178468266HCID 178468266, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Ethyl 2-chlorobenzimidate (2.80 g) and triethylamine (1.70 g) are dissolved in toluene (50 ml), to which is added dropwise (E)-3-chloro-2-methyl-2-butenoyl chloride at 5° C.-10° C. with stirring, and the stirring is continued at room temperature for 4 hours after the completion of the addition. After the completion of the reaction, the reaction mixture is added with toluene (150 ml), washed with a saline solution, dried on anhydrous magnesium sulfate and concentrated under a reduced pressure. The concentrate is purified through a silica gel column chromatography (Wakogel C-200: made by Wako Junyaku Kabushiki Kaisha) using a mixed solution of hexane-ethyl acetate (10:1) as a developing medium to obtain an oily ethyl (E)-N-(3-chloro-1-methyl-2-butenoyl)-2-chlorobenzimidate (2.37 g).

Workup

  1. additionafter the completion of the addition
  2. customAfter the completion of the reaction
  3. washwashed with a saline solution
  4. dry with materialdried on anhydrous magnesium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe concentrate is purified through a silica gel column chromatography (Wakogel C-200: made by Wako Junyaku Kabushiki Kaisha)

Sources & evidence

ORD record
ord-93dd602c15d746718811172b55d0f1cc
Source dataset
uspto-grants-1995_11
Patent number
US05466705

Reaction notes

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