Hydrochloric Acid → Hexanoic acid, 2-chlorocarbonyl-4-methyl-3-oxo-1-phenyl-pyrazolidin-4-ylmethyl ester

HRID 2214334Notes

Reaction equation

HRID 2214334 reaction equation
[C:1]([O:8][CH2:9][C:10]1([CH3:22])[CH2:14][N:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:12][C:11]1=[O:21])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(N(CC)C(C)C)(C)C.[C:32](Cl)([Cl:34])=[O:33].C1(C)C=CC=CC=1.Cl>ClCCl>[C:1]([O:8][CH2:9][C:10]1([CH3:22])[CH2:14][N:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]([C:32]([Cl:34])=[O:33])[C:11]1=[O:21])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 86227270HCID 86227270, compound

Product 1

HCID 86603516Hexanoic acid, 2-chlorocarbonyl-4-methyl-3-oxo-1-phenyl-pyrazolidin-4-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of hexanoic acid, 4-methyl-3-oxo-1-phenyl-pyrazolidin-4-ylmethyl ester (0.74 g, 0.0024 mol) and N,N-diisopropylethylamine (0.36 g, 0.0028 mol) in dichloromethane (8 ml) was added dropwise over 30 min to a stirred solution of a 20% phosgene in toluene solution (1.5 ml, 0.0028 mol) and dichloromethane (8 ml) under an atmosphere of argon. The reaction mixture was cooled using an acetone-solid carbon dioxide bath such that the initial temperature was −30° C. and the reaction remained below −20° C. during the addition. The reaction was stirred for 2 hr at between −30° C. and −20° C. Dilute aqueous hydrochloric acid (8 ml) was added to the cold reaction. The organic layer was washed with saturated aqueous sodium chloride (8 ml), dried over magnesium sulfate, and concentrated in vacuo to give a yellow viscous oil. Analysis was consistent with the desired product. The total yield of product was 0.83 g (96%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customwas −30° C.
  3. additionthe reaction remained below −20° C. during the addition
  4. washThe organic layer was washed with saturated aqueous sodium chloride (8 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a yellow viscous oil

Sources & evidence

ORD record
ord-416031a0c9024bdf9a9d59b1744b3941
Source dataset
uspto-grants-2006_09
Patent number
US07108964B2

Reaction notes

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