Acetic Acid → HCID 67042921, compound

HRID 2039534Notes

Reaction equation

HRID 2039534 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]([NH:13][C:14]3[CH:22]=[C:21]([S:23](=[O:26])(=[O:25])[NH2:24])[CH:20]=[CH:19][C:15]=3[C:16](O)=[O:17])=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1.C(O)(=O)C.C(OC(=O)C)(=O)C>C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]3[O:12][C:16](=[O:17])[C:15]4[CH:19]=[CH:20][C:21]([S:23]([NH2:24])(=[O:26])=[O:25])=[CH:22][C:14]=4[N:13]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 67042814HCID 67042814, compound

Product 1

HCID 67042921HCID 67042921, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(2-benzo[1,3]dioxol-5-yl-acetylamino)-4-sulfamoyl-benzoic acid (0.10 g, 0.26 mmol), acetic acid (1.5 mL) and acetic anhydride (0.10 mL, 1.06 mmol) was stirred at reflux for 1 h. The reaction was diluted with ethyl acetate and washed with NaHCO3 satured solution, then with water and brine. The organic phase was dried over Na2SO4, filtered and evaporated to give the 2-benzo[1,3]dioxol-5-ylmethyl-4-oxo-4H-benzo[d][1,3]oxazine-7-sulfonic acid amide intermediate (0.032 g) as yellow oil. To a solution of 2-benzo[1,3]dioxol-5-ylmethyl-4-oxo-4H-benzo[d][1,3]oxazine-7-sulfonic acid amide (0.032 g, 0.09 mmol) in dry pyridine (1 mL) was added aminoguanidine hydrogencarbonate (0.013 g, 0.098 mmol) and the mixture was heated under microwave condition at 180° C. for 1.5 h. The solvent was then evaporated and the crude was taken up in methanol to give the title compound (0.013 g, 12% yield).

Workup

  1. temperatureat reflux for 1 h
  2. washwashed with NaHCO3 satured solution
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-4ca68ed3d1514bf091c4a809cfd2e1d6
Source dataset
uspto-grants-2013_11
Patent number
US08580783B2

Reaction notes

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