Meclofenamic acid → HCID 14951346, compound

HRID 2211171Notes

Reaction equation

HRID 2211171 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([Cl:25])=[C:12]([NH:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=2[C:22](O)=[O:23])[C:13]=1[Cl:14].C[N:27](C)C=O.[OH-].[NH4+]>C(Cl)Cl.O1CCCC1>[Cl:14][C:13]1[C:8]([CH3:7])=[CH:9][CH:10]=[C:11]([Cl:25])[C:12]=1[NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=1[C:22]([NH2:27])=[O:23]

Participants

7

Reactant 4

HCID 4037Meclofenamic acidHCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 65578Oxalyl chloride

Product 1

HCID 14951346HCID 14951346, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Oxalyl chloride (1.90 g, 14.8 mmol) is added dropwise to a 0° C. suspension of meclofenamic acid (2.00 g, 6.7 mmol) and dimethylformamide (530 μl, 6.7 mmol) in 100 ml of methylene chloride. The clear yellow solution is stirred at 0° C. for one hour and then added by cannula to 3.6 ml of ammonium hydroxide (29% aqueous solution) in tetrahydrofuran at room temperature. After one hour the volatiles are removed and the residue partioned between ethyl acetate and water. The organic layer is washed with brine and dried over magnesium sulfate and concentrated. The white solid is recrystallized from ethyl acetate and isopropanol to give 1.30 g (69%), mp 185°-187° C.

Workup

  1. customAfter one hour the volatiles are removed
  2. washThe organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe white solid is recrystallized from ethyl acetate and isopropanol
  6. customto give 1.30 g (69%), mp 185°-187° C.

Sources & evidence

ORD record
ord-9d501397a88941408657bdcbde7e939b
Source dataset
uspto-grants-1995_10
Patent number
US05462952

Reaction notes

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