Triethylamine → 4-cyano-N-(4-propoxybenzyl)-N-(furan-2-ylmethyl)benzenesulfonamide

HRID 1686215Notes

Reaction equation

HRID 1686215 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[CH2:13]([O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][NH:22][CH2:23][C:24]2[O:25][CH:26]=[CH:27][CH:28]=2)=[CH:19][CH:18]=1)[CH2:14][CH3:15].C(N(CC)CC)C>C(Cl)Cl.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:22]([CH2:21][C:20]2[CH:19]=[CH:18][C:17]([O:16][CH2:13][CH2:14][CH3:15])=[CH:30][CH:29]=2)[CH2:23][C:24]2[O:25][CH:26]=[CH:27][CH:28]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 28332616(2-Furylmethyl)[(4-propoxyphenyl)methyl]amine

Product 1

HCID 602089124-cyano-N-(4-propoxybenzyl)-N-(furan-2-ylmethyl)benzenesulfonamideYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-cyanobenzene-1-sulfonyl chloride (600 mg, 2.9 mmol) was added to a stirring solution of N-(4-propoxybenzyl)-1-(furan-2-yl)methanamine (Example 5-8b) (685 mg, 2.9 mmol) and triethylamine (455 mg, 4.5 mmol) in DCM (100 mL) and the reaction was stirred for 2 hours. The reaction was diluted with H2O (200 mL) and extracted with DCM (3×, 75 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated on the rotovap. The residue was purified by silica gel chromatography (10% ethyl acetate in hexanes) to afford 4-cyano-N-(4-propoxybenzyl)-N-(furan-2-ylmethyl)benzenesulfonamide (500 mg, 50%) as an off white solid. NMR (DMSO-d6, 400 MHz): δ 0.95 (t, J=7.2 Hz, 3H), 1.70 (m, J=6.4 Hz, 2H), 3.88 (t, J=6.4 Hz, 2H), 4.25 (s, 2H), 4.28 (s, 2H), 6.15 (d, J=3.2 Hz, 1H), 6.27 (m, 1H), 6.84 (d, J=6.8 Hz, 2H), 7.11 (d, J=8.8 Hz, 2H), 7.39 (m, 1H), 7.93 (d, J=6.4 Hz, 2H), 8.01 (d, J=6.4 Hz, 2H).

Workup

  1. extractionextracted with DCM (3×, 75 mL)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated on the rotovap
  5. customThe residue was purified by silica gel chromatography (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b9ee2076a05045a9a44ef6ff760dde6c
Source dataset
uspto-grants-2012_04
Patent number
US08148544B2

Reaction notes

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