Sulfanilamide → HCID 55210129, compound

HRID 624354Notes

Reaction equation

HRID 624354 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[O:12]1[CH2:17][CH2:16][CH:15]([CH:18]=O)[CH2:14][CH2:13]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.C(O)(=O)C>[O:12]1[CH2:17][CH2:16][CH:15]([CH2:18][NH:1][C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:9])=[O:10])=[CH:4][CH:3]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 5333SulfanilamideHCID 5049666Sodium triacetoxyborohydrideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehyde

Product 1

HCID 55210129HCID 55210129, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Aminobenzenesulfonamide (6.80 g), tetrahydropyran-4-carboxaldehyde (4.96 g), and sodium triacetoxyborohydride (16.74 g) in tetrahydrofuran (300 mL) and acetic acid (15 mL) were stirred at room temperature for 24 hours. The reaction was concentrated and taken up in ethyl acetate. The resulting solution was washed with water and brine, concentrated, and chromatographed on silica gel with 50% ethyl acetate/hexanes.

Workup

  1. concentrationThe reaction was concentrated
  2. washThe resulting solution was washed with water and brine
  3. concentrationconcentrated
  4. customchromatographed on silica gel with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e00a694192e44a86b113b2bf9e6cb126
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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