Sulfamic Acid → HCID 89725527, compound

HRID 1480533Notes

Reaction equation

HRID 1480533 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][C:7]=2[CH:16]=1)=[O:2].S(=O)(=O)([OH:19])N.Cl([O-])=O.[Na+]>C1COCC1.CC(O)(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][CH3:15])=[O:12])=[CH:8][C:7]=2[CH:16]=1)([OH:19])=[O:2]

Participants

7

Reactant 3

HCID 5987Sulfamic Acid2×HCID 13343417HCID 13343417, compoundHCID 23668197Sodium Chlorite2×

Product 1

HCID 89725527HCID 89725527, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-formylbenzofuran-2-carboxylate (3.8 g, 17.4 mmol) was dissolved in a mixture of THF (80 mL) and t-BuOH (20 mL). A solution of sulfamic acid (4.0 g, 41.2 mmol) and sodium chlorite (3.4 g, 37.6 mmol) in water (70 mL) was added dropwise at RT. After 3 h an additional portion of sulfamic acid (1.2 g) and sodium chlorite (1.4 g) in water was added in one portion. The reaction mixture was stirred overnight at RT, then extracted twice with EtOAc, dried over sodium sulfate and concentrated under vacuum to give the crude product, 4.87 g which was suitable for use without purification. 1H NMR (DMSO-d6) 8.42 (m, 1H), 8.07 (m, 1H), 7.49-7.81 (m, 2H), 4.37 (q, 2H, OCH2), 1.34 (t, 3H, OCH2CH3); m/z 234.94 [M+H]+.

Workup

  1. extractionextracted twice with EtOAc
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6f7a6a71e97e461a8b0b11c3b466e66f
Source dataset
uspto-grants-2016_08
Patent number
US09409884B2

Reaction notes

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