3,5-Dichloro-2-hydroxybenzenesulphonyl chloride → HCID 58531699, compound

HRID 1889704Notes

Reaction equation

HRID 1889704 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH:9]=2)=[CH:4][CH:3]=1.[Cl:24][C:25]1[C:26]([OH:36])=[C:27]([S:32](Cl)(=[O:34])=[O:33])[CH:28]=[C:29]([Cl:31])[CH:30]=1>C1COCC1>[Cl:24][C:25]1[C:26]([OH:36])=[C:27]([S:32]([N:15]([CH2:14][C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:13]=[CH:12][CH:11]=2)[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)(=[O:34])=[O:33])[CH:28]=[C:29]([Cl:31])[CH:30]=1

Participants

4

Reactant 2

HCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 58531372HCID 58531372, compound

Product 1

HCID 58531699HCID 58531699, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4′-chlorobiphenyl-3-yl)-N-(4-fluorobenzyl)methanamine (70 mg, 0.22 mmol) in THF (4 mL) were added 3,5-dichloro-2-hydroxybenzenesulfonyl chloride (61.8 mg, 0.24 mmol) and TEA (0.08 mL, 0.54 mmol). The resulting mixture was stirred at rt for 1 h and concentrated in vacuo. The residue was dissolved in MeOH and purified by preparative HPLC. Fractions containing the desired product were combined, concentrated, and lyophilized to give the title compound (46 mg, 39%) as a glassy solid. 1H NMR (CD3OD) 7.59 (d, J=4.0 Hz, 1H), 7.43 (d, J=4.0 Hz, 1H), 7.36-7.35 (m, 5H), 7.22 (t, J=8.0 Hz, 1H), 7.16-7.09 (m, 5H), 7.05-7.03 (t, J=8.0 Hz, 1H), 6.90-6.85 (m, 2H), 4.46 (s, 2H), 4.41 (s, 2H). MS (ESI): 550.0 (M−H)−.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in MeOH
  3. custompurified by preparative HPLC
  4. additionFractions containing the desired product
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4d523c7f4cbb469eb8f83efd88749722
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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