Sulfamic Acid → HCID 54167058, compound

HRID 419303Notes

Reaction equation

HRID 419303 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7])=[O:2].S(=O)(=O)([OH:17])N.Cl([O-])=O.[Na+].CCOC(C)=O>O1CCOCC1.O>[CH3:14][O:13][C:12]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:1]([OH:17])=[O:2]

Participants

7

Reactant 4

HCID 5987Sulfamic AcidHCID 8857Ethyl AcetateHCID 15192109Methyl 3-formyl-4-methoxybenzoateHCID 23668197Sodium Chlorite

Product 1

HCID 54167058HCID 54167058, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

Crude methyl 3-formyl-4-(methyloxy)benzoate from the previous step was dissolved in 40 mL of dioxane with stirring. Sulfamic acid (5.87 g, 60.5 mmol) in 20 mL of H2O was added to the stirring solution. Sodium chlorite (1.68 g, 80% by weight, 18.6 mmol) in 20 mL of H2O was added dropwise via addition funnel. The reaction was stirred for 40 min and poured into EtOAc and H2O. The layers were separated, and the organic layer was washed with brine. The combined aqueous layers were extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The solid was transferred to an Erlenmeyer flask with the aid of 30-40 mL of DCM. Approximately 50 mL of hexanes was added. Air was blown over the solution to allow most of the DCM to evaporate. Diethyl ether was added (20-30 mL), and the suspension was filtered. The solid was washed with hexanes, collected, and dried to afford 1.96 g (82% over 2 steps) of the desired compound. 1H NMR (400 MHz, DMSO-d6): δ 12.92 (br s, 1H), 8.22 (d, J=2.2 Hz, 1H), 8.07 (dd, J=8.8, 2.2 Hz, 1H), 7.24 (d, J=8.8 Hz, 1H), 3.88 (s, 3H), 3.82 (s, 3H).

Workup

  1. stirringThe reaction was stirred for 40 min
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. extractionThe combined aqueous layers were extracted with EtOAc
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. additionApproximately 50 mL of hexanes was added
  9. customto evaporate
  10. additionDiethyl ether was added (20-30 mL)
  11. filtrationthe suspension was filtered
  12. washThe solid was washed with hexanes
  13. customcollected
  14. customdried

Sources & evidence

ORD record
ord-01b2738eda8546eaa80a86f3000e57ad
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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