Sodium hydride → 2-Chloro-N-[3,5-dichloro-4-(6-nitro-benzothiazol-2-yloxy)-phenyl]4-trifluoromethyl-benzenesulfonamide

HRID 1819814Notes

Reaction equation

HRID 1819814 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[S:12]([NH:15][C:16]1[CH:21]=[C:20]([Cl:22])[C:19]([OH:23])=[C:18]([Cl:24])[CH:17]=1)(=[O:14])=[O:13].[H-].[Na+].Cl[C:28]1[S:29][C:30]2[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[CH:33][C:31]=2[N:32]=1>CN(C=O)C.CCOC(C)=O.Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[S:12]([NH:15][C:16]1[CH:21]=[C:20]([Cl:22])[C:19]([O:23][C:28]2[S:29][C:30]3[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[CH:33][C:31]=3[N:32]=2)=[C:18]([Cl:24])[CH:17]=1)(=[O:13])=[O:14]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 754762-Chloro-6-nitrobenzothiazoleHCID 18511514HCID 18511514, compound

Product 1

HCID 185115282-Chloro-N-[3,5-dichloro-4-(6-nitro-benzothiazol-2-yloxy)-phenyl]4-trifluoromethyl-benzenesulfonamideYield 74%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-N-(3,5-dichloro-4-hydroxy-phenyl)-4-trifluoromethyl-benzenesulfonamide (421, 1.52 g, 3.41 mmol) in 10 mL of DMF, was added NaH (Aldrich, 288 mg, 60%, 7.2 mmol). The mixture was stirred for 10 min, then 2-chloro-6-nitrobenzothiazole (411, 765 mg, 3.56 mmol) was added. The reaction mixture was stirred until no 421 remained by TLC. The mixture was diluted with EtOAc and 2N HCl, extracted 3× with EtOAc (100 mL). The organic layers were washed twice with a brine solution (100 mL), dried over Na2SO4 and concentrated. The residue was purified by chromatography (15%-20% EtOAc/hexanes) to give 1.5 g (74%) of product. 1H NMR (400 MHz, DMSO-d6) δ 11.69 (s, 1H), 9.08 (d, J=2.4 Hz, 1H), 8.38 (d, J=8.3 Hz, 1H), 8.26 (dd, J=9.0, 2.4 Hz, 1H), 8.22 (s, 1H), 8.00 (d, J=8.4 Hz, 1H), 7.87 (d, J=9.0 Hz, 1H), 7.33 (s, 2H). MS (EI): m/z 596 (M−H).

Workup

  1. stirringThe reaction mixture was stirred until no 421
  2. extractionextracted 3× with EtOAc (100 mL)
  3. washThe organic layers were washed twice with a brine solution (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (15%-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-fc229a99a5924bf7b1c18089db947c99
Source dataset
uspto-grants-2009_10
Patent number
US07601841B2

Reaction notes

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