1,2-Dichloroethane → 3,5-dimethyl-N-(4-chloro-3-iodophenyl)isoxazole-4-carboxamide

HRID 632978Notes

Reaction equation

HRID 632978 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[I:9].[CH3:10][C:11]1[C:15]([C:16](O)=[O:17])=[C:14]([CH3:19])[O:13][N:12]=1.C(Cl)CCl>CN(C1C=CN=CC=1)C>[CH3:10][C:11]1[C:15]([C:16]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([Cl:1])=[C:3]([I:9])[CH:4]=2)=[O:17])=[C:14]([CH3:19])[O:13][N:12]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 756363,5-Dimethylisoxazole-4-carboxylic acidHCID 218749544-Chloro-3-iodoaniline

Product 1

HCID 668780383,5-dimethyl-N-(4-chloro-3-iodophenyl)isoxazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

4-Chloro-3-iodoaniline (1.01 g, 4 mmol) was used in procedure E with 3,5-dimethyl-4-isoxazolecarboxylic acid (0.565 g, 4 mmol), EDC (1.32 g, 6.8 mmol), TEA (0.5 mL), DMAP (50 mg, 0.4 mmol) at 23° C. for overnight. The crude reaction was purified by silica gel chromatography (0-15% ethyl acetate/CH2Cl2) to yield 3,5-dimethyl-N-(4-chloro-3-iodophenyl)isoxazole-4-carboxamide as a white solid.

Workup

  1. customThe crude reaction
  2. customwas purified by silica gel chromatography (0-15% ethyl acetate/CH2Cl2)

Sources & evidence

ORD record
ord-e5dae171b823496d8175e66fa218e362
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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