Isobutylamine → HCID 520070, compound

HRID 1791013Notes

Reaction equation

HRID 1791013 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].C(N(CC)CC)C.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[CH2:1]([NH:5][S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 7369Benzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 520070HCID 520070, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4.14 g of isobutylamine (56.6 mmol) and 2.86 g of triethylamine (28.3 mmol) in 40 mL of CH2Cl2 was slowly added 5.0 g of benzenesulfonyl chloride (28.3 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 30 min and then at rt for 1 hr. 150 mL of CH2Cl2 were added, and the organic layer was washed with saturated aqueous solution of NH4Cl and brine (30×2 mL), dried over MgSO4, filtered, and the filtrate was concentrated to give the title compound. 1H NMR (CDCl3) δ 0.87 (d, J=6.6 Hz, 6H), 1.71 (tsept, J=6.7, 6.5 Hz, 1H), 2.76 (dd, J=6.5, 6.7 Hz, 2H), 4.61 (t, J=6.5 Hz, 1H), 7.49–7.88 (m, 5H). Mass Spectrum (CI+) m/e=214 (M+1).

Workup

  1. customat 0° C
  2. waitat rt for 1 hr
  3. washthe organic layer was washed with saturated aqueous solution of NH4Cl and brine (30×2 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ab4cba9ad83843d2a764bfbec7274330
Source dataset
uspto-grants-2006_07
Patent number
US07071358B2

Reaction notes

Loading…