Ethanolamine → HCID 22051136, compound

HRID 1832097Notes

Reaction equation

HRID 1832097 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 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-3fb06fd3ed074688b76caf8bd6080c69
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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