HCID 67042601, compound → HCID 67042999, compound

HRID 2039524Notes

Reaction equation

HRID 2039524 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([CH2:8][C:9]2O[C:13](=O)[C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)(O)O.[NH2:26][NH:27][C:28]([NH2:30])=[NH:29]>N1C=CC=CC=1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([CH2:8][C:9]2[N:26]3[N:27]=[C:28]([NH2:30])[N:29]=[C:13]3[C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 67042601HCID 67042601, compoundHCID 178513185HCID 178513185, compound

Product 1

HCID 67042999HCID 67042999, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(4-nitrobenzyl)-4H-3,1-benzoxazin-4-one (5.7 g, 20.2 mmol) and aminoguanidine hydrogencarbonate (2.7 g, 20.2 mmol) in pyridine (25 mL) was heated under microwave condition at 180° C. for 30 minutes. After cooling, the red solution was taken up in ethyl acetate, washed with brine and dried over Na2SO4. The solvent was removed in vacuum and the residue was chromatographed on silica gel eluting with DCM/CH3OH 95/5 to furnish the title compound (2.7 g, 42% yield)

Workup

  1. temperatureAfter cooling
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed in vacuum
  5. customthe residue was chromatographed on silica gel eluting with DCM/CH3OH 95/5

Sources & evidence

ORD record
ord-934c5b99ae254ceeae443c6da06d8c99
Source dataset
uspto-grants-2013_11
Patent number
US08580783B2

Reaction notes

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