Methanol → 1-[3-(5-Bromo-thien-2-yl)-4,5-dihydro-isoxazol-5-ylmethyl]-4-methyl-1H-1,2,3-triazole

HRID 747201Notes

Reaction equation

HRID 747201 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[CH2:11][CH:10](NC)[O:9][N:8]=2)=[CH:4][CH:3]=1.[CH:14]([N:17](C(C)C)CC)(C)C.CO.Cl[CH:26](Cl)[C:27](=[N:29][NH:30]S(C1C=CC(C)=CC=1)(=O)=O)[CH3:28]>C(OCC)(=O)C>[Br:1][C:2]1[S:6][C:5]([C:7]2[CH2:11][CH:10]([CH2:14][N:17]3[CH:26]=[C:27]([CH3:28])[N:29]=[N:30]3)[O:9][N:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 17954483[3-(5-Bromo-thien-2-yl)-4,5-dihydro-isoxazol-5-yl]-methylamineHCID 73181071N'-[2,2-dichloro-1-methylethylidene]-4-methylbenzenesulfonohydrazide

Product 1

HCID 597495191-[3-(5-Bromo-thien-2-yl)-4,5-dihydro-isoxazol-5-ylmethyl]-4-methyl-1H-1,2,3-triazoleYield 28.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

[3-(5-Bromo-thien-2-yl)-4,5-dihydro-isoxazol-5-yl]-methylamine (2.2 g, 8.4 mmol) and diisopropylethylamine (7.3 ml, 42 mmol) were added to anhydrous methanol (50 ml) followed by addition of N′-[2,2-dichloro-1-methylethylidene]-4-methylbenzenesulfonohydrazide (3.2 g, 10.9 mmol). The reaction was stirred at room temperature for four hours and then ethyl acetate was added. The precipitate was collected and washed with water (2×25 ml) to give the desired product (793 mg).

Workup

  1. customThe precipitate was collected
  2. washwashed with water (2×25 ml)

Sources & evidence

ORD record
ord-62c311fa1dbc4df8b3731b88aa8a625a
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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