Water → HCID 59350344, compound

HRID 2271385Notes

Reaction equation

HRID 2271385 reaction equation
[CH2:1]([NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)(=[O:10])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([S:33](Cl)(=[O:35])=[O:34])[CH:28]=[CH:29][C:30]=1[O:31][CH3:32].O>CN(C=O)C>[CH3:20][O:19][C:13]1[CH:12]=[C:11]([S:8]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[S:33]([C:27]2[CH:28]=[CH:29][C:30]([O:31][CH3:32])=[C:25]([O:24][CH3:23])[CH:26]=2)(=[O:35])=[O:34])(=[O:10])=[O:9])[CH:16]=[CH:15][C:14]=1[O:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 3243273HCID 3243273, compound

Product 1

HCID 59350344HCID 59350344, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stiffing solution of N-hexyl-3,4-dimethoxybenzenesulfonamide (0.250 g, 0.830 mmol) in 3.30 mL of DMF, NaH (0.037 g, 0.913 mmol; 60% in oil dispersion) was added. After 30 mins, 3,4-dimethoxybenzenesulfonyl chloride (0.222 g, 0.937 mmol) was added. After a further 1 hr, the reaction solution was poured over water (15 mL) forming a white solid. The solid was filtered and recrystallized from methanol to afford 0.103 g (25%) of N-(3,4-dimethoxyphenylsulfonyl)-N-hexyl-3,4-dimethoxybenzenesulfonamide as a white solid. 1H NMR (acetone-d6, 400 MHz) δ 7.62 (dd, J=2.9, 8.2 Hz, 2H), 7.57 (d, J=2.3 Hz, 2H), 6.94 (d, J=8.6 Hz, 2H), 3.95 (s, 12H), 3.60 (m, 2H), 1.63 (m, 2H), 1.21 (m, 6H), 0.85 (t, J=6.8 Hz, 3H); 13C NMR (acetone-d6, 100 MHz) δ 150.05, 144.99, 131.10, 121.34, 115.05, 115.00, 49.00, 31.65, 26.38, 22.45, 13.51.

Workup

  1. waitAfter a further 1 hr
  2. customforming a white solid
  3. filtrationThe solid was filtered
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-a3ccc1ec52cd4d69a4dcabed2fe575c9
Source dataset
uspto-grants-2015_09
Patent number
US09120744B2

Reaction notes

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