Hydrochloric Acid → HCID 19815176, compound

HRID 465972Notes

Reaction equation

HRID 465972 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:19])=[C:6]([NH:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[C:16]([O-:18])=O)[C:7]=1[Cl:8].[Na+].CN(C=O)C.C(Cl)(=O)C(Cl)=O.[CH2:32]([NH:39][OH:40])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl>C(Cl)Cl.C1COCC1.CCN(CC)CC.O>[Cl:8][C:7]1[C:2]([CH3:1])=[CH:3][CH:4]=[C:5]([Cl:19])[C:6]=1[NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=1[C:16]([N:39]([OH:40])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:18]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 4038Meclofenamate SodiumHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2794173Benzylhydroxylamine

Product 1

HCID 19815176HCID 19815176, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Meclomen (5.92 g; 0.02 mol) is suspended in CH2Cl2 (150 ml) containing DMF (1.46 g, 0.02 mol) and cooled to 0° C. Oxalyl chloride is added to the solution over 30 minutes and the resulting yellow solution is stirred at 24° C. for 20 hours and then added to a cold solution of N-benzylhydroxylamine (2.46 g; 0.02 mol) in THF (60 ml)--H2O (15 ml)--Et3N (20 ml) mixture. The solution is allowed to come to 24° C. and treated with 2N HCl (160 ml). The product is extracted with CH2Cl2. The extracts are dried over sodium sulfate and evaporated to dryness. The residue is flash chromatographed through SiO2 gel eluting with CH2Cl2. The fractions containing the product are evaporated and the solid residue is recrystallized from isopropylether/n-hexane yielding white crystals. Yield 1.45 g (18.6%); mp 133°-135° C.

Workup

  1. customto come to 24° C.
  2. extractionThe product is extracted with CH2Cl2
  3. dry with materialThe extracts are dried over sodium sulfate
  4. customevaporated to dryness
  5. customchromatographed through SiO2 gel
  6. washeluting with CH2Cl2
  7. additionThe fractions containing the product
  8. customare evaporated
  9. customthe solid residue is recrystallized from isopropylether/n-hexane yielding white crystals

Sources & evidence

ORD record
ord-ba7ab05223d54a34997d41949e74e8da
Source dataset
uspto-grants-1992_10
Patent number
US05155110

Reaction notes

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