Sulfamic Acid → HCID 18668891, compound

HRID 1058576Notes

Reaction equation

HRID 1058576 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])=[CH:8][C:7]=2[CH:21]=1)=[O:2].Cl([O-])=[O:23].[Na+].S(=O)(=O)(O)N>C1COCC1.C(O)(C)(C)C.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:12])=[CH:8][C:7]=2[CH:21]=1)([OH:23])=[O:2]

Participants

7

Reactant 3

HCID 5987Sulfamic AcidHCID 18668849HCID 18668849, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 18668891HCID 18668891, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 5-formylbenzofuran-2-carboxylate (0.380 g, 0.1.36 mmol) in THF (5 mL) and t-butanol (1 mL) was added slowly a solution of sodium chlorite (0.245 g 2.71 mmol) and sulfamic acid (0.277 g, 2.86 mmol) in water (2 mL). After stirring at room temperature for 3 h, the solution was partitioned between ethyl acetate and water. The organic layer was washed successively with water, saturated aqueous sodium bicarbonate, and brine then collected, dried (MgSO4), filtered and concentrated to yield the title compound as an off-white solid (0.272 g, 68%). 1 H NMR (400 MHz, CDCl3) δ 8.52 (s, 1H), 8.23 (d, 1H), 7.67 (m, 2H), 7.49 (m, 2H), 7.41 (m, 3H), 5.46 (s, 2H).

Workup

  1. customthe solution was partitioned between ethyl acetate and water
  2. washThe organic layer was washed successively with water, saturated aqueous sodium bicarbonate, and brine
  3. customthen collected
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b9ffab51ba0e41b58430ac4e256ab507
Source dataset
uspto-grants-2003_02
Patent number
US06518267B1

Reaction notes

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