Ethanolamine → Methanesulfonic acid 8-(2-hydroxyacetylamino)naphthalen-2-yl ester

HRID 1861999Notes

Reaction equation

HRID 1861999 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH:14]=[C:13]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=[CH:11]2)=[O:4].C(CN)[OH:22]>C(OC(C)=O)(C)C>[OH:22][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH:14]=[C:13]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=[CH:11]2)=[O:4]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 155493251-(Chloroacetamido)-7-[(methanesulfonyl)oxy]naphthalene

Product 1

HCID 88118569Methanesulfonic acid 8-(2-hydroxyacetylamino)naphthalen-2-yl ester

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

To a solution of ester from Step B (11.0 g, 39.5 mmol) in 150 mL of i-PrOAc at room temperature was added ethanolamine (12.0 mL, 199 mmol). After 18 hours, the reaction was partitioned between EtOAc and water, and the organic layer was extracted with saturated brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide a dark oil.

Workup

  1. customthe reaction was partitioned between EtOAc and water
  2. extractionthe organic layer was extracted with saturated brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a dark oil

Sources & evidence

ORD record
ord-fb6d84caeb864c26a6a86166673ff955
Source dataset
uspto-grants-2003_03
Patent number
US06534506B2

Reaction notes

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