Diethyl Ether → HCID 44128897, compound

HRID 2098308Notes

Reaction equation

HRID 2098308 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][N:10]=[C:11]=[O:12])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[N+:13](=[C:15]1[N:19]=[CH:18][N:17]=[C:16]1[C:20]([NH2:22])=[O:21])=[N-:14].CCOCC>CCOC(C)=O.CS(C)=O>[CH2:6]([O:5][P:4]([CH2:9][N:10]1[C:11](=[O:12])[N:19]2[CH:18]=[N:17][C:16]([C:20](=[O:21])[NH2:22])=[C:15]2[N:13]=[N:14]1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 15739370Diethyl (isocyanatomethyl)phosphonateHCID 534265854-Diazo-4H-imidazole-5-carboxamide

Product 1

HCID 44128897HCID 44128897, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Isocyanatomethyl-phosphonic acid diethyl ester (953 mg, 6.95 mmol) in EtOAc (10 mL) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (0.5 g, 3.65 mmol) in dry dimethylsulfoxide (10 mL) at room temperature under nitrogen. The resulting mixture was stirred at room temperature for 16 hours. The mixture was poured into Et2O and the resultant collected by filtration and washed with Et2O (3 reaction volumes) and dried to give the title compound as a solid (1.14 g, 50%). 1H NMR (400 MHz, d6-DMSO) δ ppm: 8.91 (1H, s), 7.88 (1H, s), 7.74 (1H, s), 4.85 (2H, t, J=11.2 Hz), 4.12 (4H, m), 1.25 (6H, t, 7.2).

Workup

  1. filtrationthe resultant collected by filtration
  2. washwashed with Et2O (3 reaction volumes)
  3. customdried

Sources & evidence

ORD record
ord-4935e962477b458d8fefc144d6e0e52b
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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