Sulfanilamide → HCID 55210129, compound

HRID 1520572Notes

Reaction equation

HRID 1520572 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 in 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-521ce4e179ec41e8a59cb616c2b12fa9
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

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