Hexylamine → HCID 3243273, compound

HRID 2271384Notes

Reaction equation

HRID 2271384 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11](Cl)(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.[CH2:22]([NH2:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(OCC)(=O)C>[CH2:22]([NH:28][S:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:13])=[O:12])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 8102HexylamineHCID 8471TriethylamineHCID 27341833,4-Dimethoxybenzenesulfonyl chloride

Product 1

HCID 3243273HCID 3243273, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,4-dimethoxybenzenesulfonyl chloride (0.500 g, 2.11 mmol), triethylamine (0.750 mL, 5.30 mmol) in 7 mL of ethyl acetate, hexylamine (0.280 mL, 2.11 mmol) was added dropwise and the resulting solution was stirred overnight. The reaction mixture was filtered and the filtrate was washed 1N HCl (2×), dried with MgSO4, filtered and concentrated in vacuo to afford 0.480 g (75%) of N-hexyl-3,4-dimethoxybenzenesulfonamide as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.46 (m, 1H), 7.32 (m, 1H), 6.94 (m, 1H), 4.22 (m, 1H), 3.93 (s, 3H), 3.92 (s, 3H), 2.93 (q, J=6.4 Hz, 2H), 1.44 (quintet, J=6.9 Hz, 2H), 1.25 (m, 6H), 0.84 (t, J=6.9 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate was washed 1N HCl (2×)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-89befef5af27451b9069002b35f0c443
Source dataset
uspto-grants-2015_09
Patent number
US09120744B2

Reaction notes

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