Ethanolamine → 5-(Dimethylamino)-N-(2-hydroxyethyl)naphthalene-1-sulfonamide

HRID 547864Notes

Reaction equation

HRID 547864 reaction equation
[S:1](Cl)([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH2:18]([CH2:20][NH2:21])[OH:19].C(N(CC)CC)C>C(Cl)Cl>[CH3:11][N:10]([CH3:12])[C:9]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:8]=1[CH:7]=[CH:6][CH:5]=[C:4]2[S:1]([NH:21][CH2:20][CH2:18][OH:19])(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 11801Dansyl chloride

Product 1

HCID 129107205-(Dimethylamino)-N-(2-hydroxyethyl)naphthalene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Under nitrogen, dansyl chloride (5.05 g, 18.72 mmol) was placed in a dry 250 mL round bottom flask equipped with a stir bar. Dry methylene chloride (50 mL) was added via syringe, the flask attached to an addition funnel and the system cooled to 0° C. Ethanolamine (1.25 g, 1.24 mL, 20.59 mmol), triethylamine (2.27 g, 3.13 mL, 22.46 mmol), and 75 mL of dry methylene chloride were loaded into the addition funnel, and the solution was added dropwise with stirring over 30 min. The solution was stirred for an additional 30 min before the ice bath was removed, the solution allowed to reach ambient temperature and left to stir for an additional 14 hours.

Workup

  1. customequipped with a stir bar
  2. customthe flask attached to an addition funnel
  3. additionthe solution was added dropwise
  4. customwas removed
  5. customto reach ambient temperature
  6. waitleft
  7. stirringto stir for an additional 14 hours

Sources & evidence

ORD record
ord-12aa739ead1f40828c021d8b39325565
Source dataset
uspto-grants-2011_05
Patent number
US07939621B2

Reaction notes

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