1,1'-Carbonyldiimidazole → HCID 58332209, compound

HRID 1891413Notes

Reaction equation

HRID 1891413 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7](=[N:18][OH:19])[NH:8][CH2:9][C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[CH3:17])[O:4][N:3]=1.C1N=CN([C:25](N2C=NC=C2)=[O:26])C=1>C1COCC1>[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[N:8]([CH2:9][C:10]3[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=3[CH3:17])[C:25](=[O:26])[O:19][N:18]=2)[O:4][N:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178425378HCID 178425378, compound

Product 1

HCID 58332209HCID 58332209, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

3-Amino-N-(5-chloro-2-methylbenzyl)-N′-hydroxyisoxazole-5-carboximidamide (0.320 g, 1.14 mmol) was dissolved in anhydrous THF (6 mL) followed by addition of N,N-carbonyldiimidazole (0.203 g, 1.25 mmol). The solution was heated at 70° C. for 1.5 h. and then concentrated and purified with silica gel chromatography (20% ethyl acetate/hexs) to give the desired product as a colorless oil (200 mg, 57%). LCMS calculated for C13H12ClN4O3(M+H)+: m/z=307.1.

Workup

  1. concentrationconcentrated
  2. custompurified with silica gel chromatography (20% ethyl acetate/hexs)

Sources & evidence

ORD record
ord-8b3fe1286a1e4ac080e1f6010f4a92a6
Source dataset
uspto-grants-2013_08
Patent number
US08507541B2

Reaction notes

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