Hydrochloric Acid → HCID 18937750, compound

HRID 2293335Notes

Reaction equation

HRID 2293335 reaction equation
[CH3:1][O:2][C:3]1[CH:35]=[CH:34][C:6]([CH2:7][N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([C:18](=[O:33])[C:19]3[CH:24]=[CH:23][C:22]([CH:25](OC)[O:26]C)=[CH:21][C:20]=3[N+:30]([O-:32])=[O:31])[N:10]=[N:9]2)=[CH:5][CH:4]=1.Cl>O1CCCC1>[CH:25]([C:22]1[CH:23]=[CH:24][C:19]([C:18]([C:11]2[N:10]=[N:9][N:8]([CH2:7][C:6]3[CH:34]=[CH:35][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:33])=[C:20]([N+:30]([O-:32])=[O:31])[CH:21]=1)=[O:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18937705HCID 18937705, compound

Product 1

HCID 18937750HCID 18937750, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-(4-methoxybenzyl)-4-(4-dimethoxymethyl-2-nitrobenzoyl)-1,2,3-triazole-5-carboxylate (7.26 g, 15 mmole) obtained in Example 11 (b-1: LP) in tetrahydrofuran (50 ml) was added a 1N aqueous hydrochloric acid solution (30 ml), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution. The solvent was removed under reduced pressure to give ethyl 4-(4-formyl-2-nitrobenzoyl)-1-(4-methoxybenzyl)1,2,3-triazole-5-carboxylate as a yellow crystalline powder (6.2 g, 94%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c993a7fb63414a69a9812100995a4f06
Source dataset
uspto-grants-1997_11
Patent number
US05686442

Reaction notes

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