Triethylamine → 3,5-Dichloro-N-((4',6-dichlorobiphenyl-3-yl)methyl)-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamide

HRID 1889715Notes

Reaction equation

HRID 1889715 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([CH2:15][NH:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:32][C:33]1[C:34]([OH:44])=[C:35]([S:40](Cl)(=[O:42])=[O:41])[CH:36]=[C:37]([Cl:39])[CH:38]=1>C(Cl)Cl>[Cl:32][C:33]1[C:34]([OH:44])=[C:35]([S:40]([N:16]([CH2:15][C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:13]([Cl:14])=[CH:12][CH:11]=2)[CH2:17][C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)(=[O:42])=[O:41])[CH:36]=[C:37]([Cl:39])[CH:38]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 585316631-(4',6-Dichlorobiphenyl-3-yl)-N-(4-fluorobenzyl)methanamine

Product 1

HCID 585313933,5-Dichloro-N-((4',6-dichlorobiphenyl-3-yl)methyl)-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamideYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1-(4′,6-Dichlorobiphenyl-3-yl)-N-(4-fluorobenzyl)methanamine (200 mg, 0.555 mmol, 1.0 eq) was dissolved in dry DCM and the resulting solution was stirred for 10 minutes and cooled to 0° C. Triethylamine (168 mg, 1.6 mmol, 3 eq) was added to the above solution and the mixture was stirred for 10 minutes. 3,5-Dichloro-2-hydroxybenzene-1-sulfonyl chloride dissolved in DCM was added slowly over a period of 10 minutes and the mixture was stirred for 4 h at ambient temperature. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel (60-120) eluting with 5-10% ethyl acetate/hexane to give the title compound (0.14 g, 46%). 1H NMR (400 MHz, CD3OD) δ 4.47 (s, 2H), 4.53 (s, 2H), 6.91-6.98 (m, 3H), 7.12-7.15 (m, 1H), 7.22-7.27 (m, 4H), 7.33-7.35 (d, 1H), 7.43-7.45 (d, 2H), 7.54 (d, 1H), 7.67 (d, 1H). MS (ESI): 583.8 (M−H)−.

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. additionwas added slowly over a period of 10 minutes
  3. stirringthe mixture was stirred for 4 h at ambient temperature
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by flash column chromatography on silica gel (60-120)
  6. washeluting with 5-10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a92bfb03bfd44eb4bd45cd826d133a83
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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