Water → HCID 22246914, compound

HRID 1595834Notes

Reaction equation

HRID 1595834 reaction equation
[CH2:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].O>C(Cl)Cl>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 40298714-Butylbenzylamine

Product 1

HCID 22246914HCID 22246914, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-butylbenzylamine (4.01 g, 24.6 mmol) in CH2Cl2 (75 mL) was added pyridine (4.0 mL, 49 mmol) followed by dropwise addition of methanesulfonyl chloride (2.5 mL, 32.3 mmol). The reaction was stirred at room temperature for 24 h and water was added. The product was extracted into CH2Cl2 (2×) and the organic solution was dried (MgSO4), filtered, and concentrated. Flash chromatography (2:1 to 1:1 hexanes:EtOAc) provided the title compound as a white solid (3.4114 g). 1H NMR (400 MHz, CDCl3) δ 7.23 (d, 2H), 7.15 (d, 2H), 4.84 (m, 1H), 4.25 (d, 2H), 2.82 (s, 3H), 2.58 (t, 2H), 1.56 (m, 2H), 1.33 (m, 2H), 0.91 (t, 3H).

Workup

  1. extractionThe product was extracted into CH2Cl2 (2×)
  2. dry with materialthe organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a304cf5ed65c485381636817aeabc0dd
Source dataset
uspto-grants-2001_09
Patent number
US06288120B1

Reaction notes

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