Triethylamine → HCID 178468279, compound

HRID 516494Notes

Reaction equation

HRID 516494 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[NH:10])[O-:9])=[CH:4][CH:3]=1.[CH2:11](N(CC)CC)[CH3:12].[Br:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](/[N:10]=[C:23](/[C:22]2[CH:26]=[CH:27][C:19]([Br:18])=[CH:20][CH:21]=2)\[O:24][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 685154-Bromobenzoyl chlorideHCID 204921064-Bromobenzenecarboximidate

Product 1

HCID 178468279HCID 178468279, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

4-Bromobenzenecarboximidate (25 g, 0.10 mole) is added to toluene (225 ml). Then triethylamine (25 ml, 0.17 mole) is added. The reaction mixture is stirred at room temperature for 10 minutes. 4-bromobenzoyl chloride (25 g, 0.12 mole) in toluene (25 ml) is added to the reaction mixture in 30 minutes at room temperature. After stirring the reaction mixture overnight, it is filtered and the toluene layer is concentrated. The product, 4-Bromo-N-[1-(4-bromo-phenyl)-1-ethoxy-meth-(z)-ylidene]benzamide, from the toluene concentrate is then washed with methanol (30 ml) and dried in vacuum (Yield=30 g (62%)). The product is used without further purification in the next reaction step.

Workup

  1. stirringAfter stirring the reaction mixture overnight, it
  2. filtrationis filtered
  3. concentrationthe toluene layer is concentrated
  4. concentrationThe product, 4-Bromo-N-[1-(4-bromo-phenyl)-1-ethoxy-meth-(z)-ylidene]benzamide, from the toluene concentrate
  5. washis then washed with methanol (30 ml)
  6. customdried in vacuum (Yield=30 g (62%))
  7. customThe product is used without further purification in the next reaction step

Sources & evidence

ORD record
ord-3cc8e0e24e7b472380f3582ed5e99536
Source dataset
uspto-grants-2015_08
Patent number
US09113536B2

Reaction notes

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