Triethylamine → HCID 58531629, compound

HRID 1889655Notes

Reaction equation

HRID 1889655 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1.[C:19]([C:21]1[CH:22]=[C:23]([S:27](Cl)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1)#[N:20].CCN(CC)CC.S(Cl)(Cl)(=O)=O>C1COCC1>[C:19]([C:21]1[CH:22]=[C:23]([S:27]([N:6]([CH2:5][C:4]2[CH:3]=[C:2]([Cl:1])[CH:17]=[C:16]([Cl:18])[CH:15]=2)[CH2:7][C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1)#[N:20]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 24648Sulfuryl chlorideHCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 58531427N-(3,5-Dichlorobenzyl)-1-(4-fluorophenyl)methanamine

Product 1

HCID 58531629HCID 58531629, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3,5-dichlorobenzyl)-1-(4-fluorophenyl)methanamine (1.40 g, 4.91 mmol) in THF (15 mL) was added 3-cyanobenzene-1-sulfonyl chloride (0.9 g, 4.46 mmol) and Et3N (1.22 mL, 8.93 mmol) at rt for 2 h. Additional sulfonyl chloride (0.35 g) and Et3N (0.5 mL) were added. The reaction mixture was stirred at rt for 15 h. The mixture was concentrated and the residue was diluted with ethyl acetate and 1 N HCl solution. The organic layer was separated, washed with brine, saturated aq NaHCO3 solution, dried over MgSO4, and concentrated to give a glassy material which was purified by flash silica gel column chromatography on silica gel (ISCO. Column: 24 g. Eluent: A: hexane. B: ethyl acetate. Condition: A to 25% of B (50 min gradient) to obtain the desired product as a white solid (1.8 g, 81%). 1H NMR (CDCl3): δ 8.08-8.02 (m, 2H), 7.93-7.90 (m, 1H), 7.70 (t, J=8.0 Hz, 1H), 7.25-7.24 (m, 1H), 7.13-7.09 (m, 2H), 6.98 (t, J=8.0 Hz, 2H), 6.90 (d, J=4.0 Hz, 2H), 4.38 (s, 2H), 4.30 (s, 2H); MS (ESI): [M−H]−=506.9.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with ethyl acetate and 1 N HCl solution
  3. customThe organic layer was separated
  4. washwashed with brine, saturated aq NaHCO3 solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give a glassy material which
  8. customwas purified by flash silica gel column chromatography on silica gel (ISCO

Sources & evidence

ORD record
ord-cdda134614a44fad8e4c0629a105e865
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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