Ethanolamine → HCID 59406275, compound

HRID 58055Notes

Reaction equation

HRID 58055 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[CH:5][C:6]([S:9](Cl)(=[O:11])=[O:10])=[N:7][CH:8]=1.[NH2:13][CH2:14][CH2:15][OH:16].CCN(CC)CC>C(#N)C>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([NH:13][CH2:14][CH2:15][OH:16])(=[O:11])=[O:10])=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 467388875-Bromopyridine-2-sulfonyl chloride, HCl

Product 1

HCID 59406275HCID 59406275, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 4 mL vial equipped with a magnetic stir bar were combined 5-bromopyridine-2-sulfonyl chloride hydrochloride (50 mg, 0.171 mmol), 2-aminoethanol (0.015 mL, 0.256 mmol), Et3N (0.071 mL, 0.512 mmol), and acetonitrile (1 mL). The resulting yellow solution stirred at room temperature overnight. The reaction mixture was subsequently partitioned between water (10 mL) and ethyl acetate (15 mL). The layers were separated and the aqueous layer was back-extracted with ethyl acetate (15 mL). The combined organic layers were concentrated to give the title compound as a clear liquid, which was used without further purification (55 mg).

Workup

  1. customIn a 4 mL vial equipped with a magnetic stir bar
  2. customThe reaction mixture was subsequently partitioned between water (10 mL) and ethyl acetate (15 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was back-extracted with ethyl acetate (15 mL)
  5. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-cf474c12ee78446ea5f7e28f2d3e3706
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Reaction notes

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