Ethanolamine → HCID 22051136, compound

HRID 1867133Notes

Reaction equation

HRID 1867133 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH2:13]([CH2:15][NH2:16])[OH:14].C(N(CC)C(C)C)(C)C>O1CCCC1>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:16][CH2:15][CH2:13][OH:14])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 27344094-(Bromomethyl)benzenesulfonyl chloride

Product 1

HCID 22051136HCID 22051136, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(Bromomethyl)benzenesulfonyl chloride (5.0 g, 18.6 mmol) was dissolved in tetrahydrofuran. Ethanolamine (1.1 mL, 18.6 mmol) and N,N-diisopropylethylamine (3.9 mL, 22.3 mmol) were added, and the reaction was allowed to stir at ambient temperature for 30 minutes. The reaction was concentrated to an oil that was partitioned between water and ethyl acetate and extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried over Na2SO4, and filtered. The resulting filtrate was concentrated to an oil that was a mixture of the title compound and 4-chloromethyl N-(2-hydroxyethyl)benzenesulfonamide. The resulting oil was dried in vacuo (3.7 g, 68%). ES-MS m/z 250 (M+H) and 294 (M+H).

Workup

  1. concentrationThe reaction was concentrated to an oil that
  2. customwas partitioned between water and ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe resulting filtrate was concentrated to an oil that
  8. additiona mixture of the title compound and 4-chloromethyl N-(2-hydroxyethyl)benzenesulfonamide
  9. customThe resulting oil was dried in vacuo (3.7 g, 68%)

Sources & evidence

ORD record
ord-91905acbed66445981ce8e127a38ed3c
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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