Hydrochloric Acid → 5-(Dimethylamino)-N-(2-oxoethyl)naphthalene-1-sulfonamide

HRID 926233Notes

Reaction equation

HRID 926233 reaction equation
C[O:2][CH:3](OC)[CH2:4][NH:5][S:6]([C:9]1[C:18]2[C:13](=[C:14]([N:19]([CH3:21])[CH3:20])[CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7].Cl>CO>[O:2]=[CH:3][CH2:4][NH:5][S:6]([C:9]1[C:18]2[C:13](=[C:14]([N:19]([CH3:21])[CH3:20])[CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 84426875HCID 84426875, compound

Product 1

HCID 187021755-(Dimethylamino)-N-(2-oxoethyl)naphthalene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

The acetal 11 (287 mg, 850 mop was dissolved in MeOH (1 mL) and coned HCl (0.5 mL) was added to the solution, which was stirred for 1 h at 25° C. The reaction mixture was then evaporated to dryness; the material left was dissolved in CH2Cl2 (10 mL) and the solution was washed with NaHCO3 (2 mL of a saturated aqueous solution). The organic layer was collected and was evaporated under low pressure to give the aldehyde as a light green foam, the total amount of which was used without further purification in the preparation of 12.

Workup

  1. customThe reaction mixture was then evaporated to dryness
  2. waitthe material left
  3. dissolutionwas dissolved in CH2Cl2 (10 mL)
  4. washthe solution was washed with NaHCO3 (2 mL of a saturated aqueous solution)
  5. customThe organic layer was collected
  6. customwas evaporated under low pressure

Sources & evidence

ORD record
ord-615ea1dead5a42e0b63008c3fd082021
Source dataset
uspto-grants-2016_03
Patent number
US09284343B2

Reaction notes

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