1,1'-Carbonyldiimidazole → HCID 58941893, compound

HRID 2097651Notes

Reaction equation

HRID 2097651 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:13]2[C:17]([CH2:18][CH2:19][O:20][CH3:21])=[N:16][O:15][N:14]=2)=[N:11][OH:12])[CH:5]=[CH:6][C:7]=1[F:8].C1N=CN([C:27](N2C=NC=C2)=[O:28])C=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:27](=[O:28])[O:12][N:11]=[C:10]2[C:13]2[C:17]([CH2:18][CH2:19][O:20][CH3:21])=[N:16][O:15][N:14]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178494846HCID 178494846, compound

Product 1

HCID 58941893HCID 58941893, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-4-(2-methoxyethyl)-1,2,5-oxadiazole-3-carboximidamide (2.5 g, 7.9 mmol) was dissolved in THF (44 mL) followed by addition of N,N-carbonyldiimidazole (1.5 g, 9.5 mmol). The reaction was heated to 70° C. for 1.5 h. The reaction solution was concentrated and purified by silica gel chromatography (20% ethyl acetate/hexane) to give the desired product (2.7 g, 99%). MF═C13H10ClFN4O4; LCMS calculated for C13H11ClFN4O4 (M+H)+: m/z=341.0.

Workup

  1. concentrationThe reaction solution was concentrated
  2. custompurified by silica gel chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-84e2f381316a4b889c7f616cb86f5868
Source dataset
uspto-grants-2013_05
Patent number
US08450351B2

Reaction notes

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