2-Methoxybenzoyl chloride → HCID 6736106, compound

HRID 1732041Notes

Reaction equation

HRID 1732041 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].[CH2:12]([N:14]1[CH2:18][CH:17]([NH2:19])[CH2:16][N:15]1[CH2:20][CH3:21])[CH3:13]>C1(C)C=CC=CC=1>[CH2:12]([N:14]1[CH2:18][CH:17]([NH:19][C:5](=[O:6])[C:4]2[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=2[O:2][CH3:1])[CH2:16][N:15]1[CH2:20][CH3:21])[CH3:13]

Participants

4

Reactant 2

HCID 889692-Methoxybenzoyl chlorideHCID 5591991,2-Diethyl-4-pyrazolidinamine

Product 1

HCID 6736106HCID 6736106, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 2-methoxybenzoyl chloride (3.41 g, 0.020 mole) in 50 ml of toluene was added dropwise to a stirred solution of 1,2-diethyl-4-aminopyrazolidine (2.86 g. 0.020 mole) in 100 ml of toluene. The mixture was stirred at ambient temperature for 2 hrs, and then at reflux temperature for 2 hrs. After standing for 16 hrs, the mixture was extracted with 100 ml of 10% sodium bicarbonate solution. The toluene layer was dried over magnesium sulfate and concentrated to give 4.32 g (81.6%) of oil. The liquid was distilled over magnesium sulfate, b.p. 160° C./0.020 mm Hg, to give 2.52 g of a clear, yellow oil.

Workup

  1. temperatureat reflux temperature for 2 hrs
  2. waitAfter standing for 16 hrs
  3. extractionthe mixture was extracted with 100 ml of 10% sodium bicarbonate solution
  4. dry with materialThe toluene layer was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b6fab3355bc14759aefe61768164d1eb
Source dataset
uspto-grants-1986_11
Patent number
US04624961

Reaction notes

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