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Hydrochloric Acid → HCID 69427081, compound

HRID 350311
Notes
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Reaction equation

HRID 350311 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:51])=[C:9]([CH2:11][O:12][C:13]2[CH:50]=[CH:49][C:16]([CH2:17][N:18]3[CH:22]=[C:21]([C:23]([O:25]CC)=[O:24])[C:20]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]5[N:39]=[C:40]([C:44]6[O:45][CH:46]=[CH:47][CH:48]=6)[O:41][C:42]=5[CH3:43])=[CH:32][CH:31]=4)=[N:19]3)=[CH:15][CH:14]=2)[N:10]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:51])=[C:9]([CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:17][N:18]3[CH:22]=[C:21]([C:23]([OH:25])=[O:24])[C:20]([O:28][CH2:29][C:30]4[CH:31]=[CH:32][C:33]([O:36][CH2:37][C:38]5[N:39]=[C:40]([C:44]6[O:45][CH:46]=[CH:47][CH:48]=6)[O:41][C:42]=5[CH3:43])=[CH:34][CH:35]=4)=[N:19]3)=[CH:49][CH:50]=2)[N:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69423039HCID 69423039, compound

Product 1

HCID 69427081HCID 69427081, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

After a mixture of ethyl 1-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyl]-3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyloxy]-1H-pyrazole-4-carboxylate (250 mg), 1N sodium hydroxide solution (1 ml), tetrahydrofuran (5 ml), and ethanol (5 ml) was stirred at room temperature for 2 hours, 1N hydrochloric acid (1 ml) was added to the mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The resulting colorless crystals were collected by filtration to obtain 1-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyl]-3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyloxy]-1H-pyrazole-4-carboxylic acid (230 mg, yield: 93%). This was recrystallized from acetone-hexane. Melting point: 144–145° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. filtrationThe resulting colorless crystals were collected by filtration

Sources & evidence

ORD record
ord-c6e9f011f7324a29bac7634a8832ceb4
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07179823B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes