Hydrochloric Acid → N-(2-furanylmethyl) 5-(2,4-dichloro-5-methylbenzenesulfonamido)-2-(3-chloro-5-pyridyloxy)benzamide

HRID 1532012Notes

Reaction equation

HRID 1532012 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8](=[O:24])[C:9]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=1[O:16][C:17]1[CH:18]=[C:19]([Cl:23])[CH:20]=[N:21][CH:22]=1.N1C=CC=CC=1.[Cl:31][C:32]1[CH:37]=[C:36]([Cl:38])[C:35]([CH3:39])=[CH:34][C:33]=1[S:40](Cl)(=[O:42])=[O:41].Cl>C1COCC1.C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8](=[O:24])[C:9]1[CH:14]=[C:13]([NH:15][S:40]([C:33]2[CH:34]=[C:35]([CH3:39])[C:36]([Cl:38])=[CH:37][C:32]=2[Cl:31])(=[O:42])=[O:41])[CH:12]=[CH:11][C:10]=1[O:16][C:17]1[CH:18]=[C:19]([Cl:23])[CH:20]=[N:21][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 1199142,4-Dichloro-5-methylbenzene-1-sulphonyl chlorideHCID 53712390N-(2-furanylmethyl) 5-amino-2-(3-chloro-5-pyridyloxy)benzamide

Product 1

HCID 9850932N-(2-furanylmethyl) 5-(2,4-dichloro-5-methylbenzenesulfonamido)-2-(3-chloro-5-pyridyloxy)benzamideYield 90%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a 0.2 M solution of N-(2-furanylmethyl) 5-amino-2-(3-chloro-5-pyridyloxy)benzamide (2.6 g, 7.6 mmol, prepared in Example 35.3) in a 1:1 THF/CH2Cl2 solution was added pyridine (0.67 mL, 8.3 mmol) followed by 2,4-dichloro-5-methylbenzenesulfonyl chloride (2.16 g, 8.3 mmol). The resulting mixture was stirred for 21 hr. A 1 M aqueous solution of HCl (100 mL) was added and the crude reaction mixture was extracted 3× with EtOAc (100 mL). The organic layers were combined and washed once with a brine solution (200 mL), dried over Na2SO4, and concentrated under vacuum. The crude solid was purified by chromatography (10-40% EtOAc in hexane) to yield 3.86 g (90%) of product as an off white solid.

Workup

  1. customthe crude reaction mixture
  2. extractionwas extracted 3× with EtOAc (100 mL)
  3. washwashed once with a brine solution (200 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe crude solid was purified by chromatography (10-40% EtOAc in hexane)

Sources & evidence

ORD record
ord-cf649846f1484286ade85121beb396db
Source dataset
uspto-grants-2001_03
Patent number
US06200995B1

Reaction notes

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