Water → HCID 22957230, compound

HRID 2302082Notes

Reaction equation

HRID 2302082 reaction equation
[NH2:1][C@H:2]([CH2:5][CH3:6])[CH2:3]O.[OH-].[Na+].[C:9]1([S:15](Cl)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>C1(C)C=CC=CC=1>[C:9]1([S:15]([N:1]2[CH2:3][C@H:2]2[CH2:5][CH3:6])(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 27238562-Amino-1-butanol, (-)-

Product 1

HCID 22957230HCID 22957230, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
62 °C

Procedure

Four grams of 2-(R)-aminobutanol and 7.2 grams of NaOH are suspended in toluene in a round bottom flask at ambient temperature. Benzenesulfonyl chloride (16.7 g) is added with agitation in one portion. The resulting white suspension is heated at 62° C. for 6 hours. Water (90 mL) is added and the layers are separated. The organic layer is washed with 70 ml of water, dried over magnesium sulfate and concentrated to provide 1-benzenesulfonyl-2(R)-ethylaziridine (6.7 g) as a colorless oil which is purified by flash chromatography over silica gel. MS: m/z (E1, 70EV) 212 (20%)

Workup

  1. customthe layers are separated
  2. washThe organic layer is washed with 70 ml of water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-94b4e1c660a84324bd8aafd5c2c0030b
Source dataset
uspto-grants-2002_08
Patent number
US06429315B1

Reaction notes

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