Hydrochloric Acid → 6-Chloro-pyridine-3-sulfonic Acid [3-Chloro-4-(naphthalen-2-ylsulfanyl)phenyl]-amide

HRID 2427176Notes

Reaction equation

HRID 2427176 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH2:20])[CH:5]=[C:6]([Cl:19])[C:7]=1[S:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1.N1C=CC=CC=1.[Cl:27][C:28]1[N:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1.Cl>C1COCC1>[Cl:19][C:6]1[CH:5]=[C:4]([NH:20][S:34]([C:31]2[CH:32]=[N:33][C:28]([Cl:27])=[CH:29][CH:30]=2)(=[O:36])=[O:35])[CH:3]=[CH:2][C:7]=1[S:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 221488343,5-Dichloro-4-(napthalen-2-ylsulfanyl)-phenylamine

Product 1

HCID 235152236-Chloro-pyridine-3-sulfonic Acid [3-Chloro-4-(naphthalen-2-ylsulfanyl)phenyl]-amideYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0.35M solution of 3-chloro-4-(naphthalen-2-ylsulfanyl)-phenylamine (90) (150 mg, 0.53 mmol) in THF was added pyridine (Aldrich, 0.21 mL, 2.63 mmol) followed by 6-chloro-pyridine-3-sulfonyl chloride (Qorpark, 122 mg, 0.58 mmol). The resulting mixture was stirred for 15 hours. A 1M aqueous solution of HCl (20 mL) was added and the crude reaction mixture was extracted 3× with EtOAc (50 mL). The organic layers were combined and washed twice with a brine solution (100 mL), dried over Na2SO4, and concentrated under vacuum. The crude solid was chromatographed (5-15% EtOAc in hexane) to yield 140 mg (58%) of 94 as a pale yellow solid.

Workup

  1. customthe crude reaction mixture
  2. extractionwas extracted 3× with EtOAc (50 mL)
  3. washwashed twice with a brine solution (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe crude solid was chromatographed (5-15% EtOAc in hexane)

Sources & evidence

ORD record
ord-7afcd6f99ca443fbb9437789c59fecdc
Source dataset
uspto-grants-2011_06
Patent number
US07968567B2

Reaction notes

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