Triethylamine → HCID 60208911, compound

HRID 658597Notes

Reaction equation

HRID 658597 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:15][C:16]1[CH:29]=[CH:28][C:19]([CH2:20][NH:21][CH2:22][C:23]2[O:24][CH:25]=[CH:26][CH:27]=2)=[CH:18][CH:17]=1)[CH3:14].C(N(CC)CC)C>C(Cl)Cl.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:21]([CH2:20][C:19]2[CH:18]=[CH:17][C:16]([O:15][CH2:13][CH3:14])=[CH:29][CH:28]=2)[CH2:22][C:23]2[O:24][CH:25]=[CH:26][CH:27]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 795889436096-81-0

Product 1

HCID 60208911HCID 60208911, compoundYield 68%

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-ethoxybenzyl)-1-(furan-2-yl)methanamine (Example 5-3b) (685 mg, 2.9 mmol) and triethlyamine (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-ethoxybenzyl)-N-(furan-2-ylmethyl)benzenesulfonamide (665 mg, 68%) as an off white solid. NMR (DMSO-d6, 400 MHz): δ 1.29 (t, J=7.2 Hz, 3H), 3.97 (q, J=6.8 Hz, 2H), 4.23 (s, 2H), 4.27 (s, 2H), 6.15 (d, J=3.2 Hz, 1H), 6.27 (m, 1H), 6.84 (d, J=8.8 Hz, 2H), 7.11 (d, J=8.8 Hz, 2H), 7.39 (m, 1H), 7.92 (d, J=8.4 Hz, 2H), 8.03 (d, J=8.4 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-fb96190bbee249cd977b45b1d3f16690
Source dataset
uspto-grants-2011_12
Patent number
US08076491B2

Reaction notes

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