Hydrochloric Acid → HCID 18937727, compound

HRID 2293328Notes

Reaction equation

HRID 2293328 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:35]=[CH:34][C:8]([CH2:9][N:10]2[C:14]([C:15]([O:17]CC)=[O:16])=[C:13]([C:20](=[O:33])[C:21]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([CH3:29])=[CH:23][C:22]=3[N+:30]([O-:32])=[O:31])[N:12]=[N:11]2)=[CH:7][CH:6]=1.Cl>O1CCCC1.CCOCC.O>[CH3:3][O:4][C:5]1[CH:35]=[CH:34][C:8]([CH2:9][N:10]2[C:14]([C:15]([OH:17])=[O:16])=[C:13]([C:20](=[O:33])[C:21]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([CH3:29])=[CH:23][C:22]=3[N+:30]([O-:32])=[O:31])[N:12]=[N:11]2)=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18937589HCID 18937589, compound

Product 1

HCID 18937727HCID 18937727, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 1N aqueous sodium hydroxide solution (1.1 ml) was added to a solution of ethyl 1-(4-methoxybenzyl)-4(5-methoxy-4-methyl-2-nitrobenzoyl)-1,2,3-triazole-5-carboxylate (b-1) (243 mg, 0.535 mmole) obtained in the preceding step (b) in tetrahydrofuran (6 ml), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was diluted with ether, and water was added. The aqueous layer was acidified with hydrochloric acid, it was extracted with ethyl acetate, and washed with water and a saturated aqueous saline. After the organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 1-(4-methoxybenzyl)-4(5-methoxy-4-methyl-2-nitrobenzoyl)-1,2,3-triazole-5-carboxylic acid (c-1': LP) as a pale yellow crystalline powder (204 mg, 89%). Next, 1-(4-methoxybenzyl)-4-(5-methoxy-4-methyl-2-nitrobenzoyl)-1,2,3-triazole-5-carboxylic acid (c-1': LP) (200 mg, 0.469 mmole) thus obtained was dissolved in a mixed solvent of ethanol (12 ml) and ethyl acetate

Workup

  1. additionwas added
  2. extractionwas extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5f96e1666cbb4423841934c7c9f94fe5
Source dataset
uspto-grants-1997_11
Patent number
US05686442

Reaction notes

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