Triethylamine → HCID 13746892, compound

HRID 1732040Notes

Reaction equation

HRID 1732040 reaction equation
C(N(CC)CC)C.[CH3:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH:20]=1)[C:17]([OH:19])=O)(=[O:11])=[O:10].ClC(OCC)=O.[CH2:29]([N:31]1[CH2:35][CH:34]([NH2:36])[CH2:33][N:32]1[CH2:37][CH3:38])[CH3:30]>C(Cl)Cl>[CH2:29]([N:31]1[CH2:35][CH:34]([NH:36][C:17](=[O:19])[C:16]2[CH:20]=[C:12]([S:9]([CH3:8])(=[O:10])=[O:11])[CH:13]=[CH:14][C:15]=2[O:21][CH3:22])[CH2:33][N:32]1[CH2:37][CH3:38])[CH3:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 1708405-Mesyl-o-anisic acidHCID 5591991,2-Diethyl-4-pyrazolidinamine

Product 1

HCID 13746892HCID 13746892, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Triethylamine (1.01 g, 0.010 mole) was added to a stirred mixture of 5-methylsulfonyl-2-methoxybenzoic acid (2.30 g, 0.010 mole) in 50 ml of methylene chloride. The mixture was cooled to 0° C. for 20 minutes and maintained at this temperature while ethyl chloroformate (1.09 g, 0.010 mole) was added dropwise. After another 20 minutes of stirring at 0° C., a solution of 1,2-diethyl-4-aminopyrazolidine (2.43 g, 0.010 mole) in 10 l of methylene chloride was added dropwise. The reaction mixture was allowed to come to ambient temperature and was stirred for 18 hrs. The reaction mixture was then extracted with 10% sodium bicarbonate solution, the methylene chloride layer separated and dried over magnesium sulfate. The methylene chloride solution was concentrated to give 3.90 g of a tanbrown solid which was recrystallized from water. A sulfate salt was prepared which was converted back to the free base. The solid free base that formed was recrystallized from ethanol-isopropyl ether to give 1.03 g (29%) of title compound; m.p. 123°-124° C. The compound was vacuum dried at 110° C.; the melting point was unchanged.

Workup

  1. additionwas added dropwise
  2. customto come to ambient temperature
  3. stirringwas stirred for 18 hrs
  4. extractionThe reaction mixture was then extracted with 10% sodium bicarbonate solution
  5. customthe methylene chloride layer separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe methylene chloride solution was concentrated

Sources & evidence

ORD record
ord-2c93560398f644b29a6abdb95ff1479e
Source dataset
uspto-grants-1986_11
Patent number
US04624961

Reaction notes

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