Hydrochloric Acid → HCID 178527544, compound

HRID 2427225Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([S:20][C:21]2[S:22][C:23]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][C:24]=3[N:25]=2)=[C:15]([Cl:32])[CH:14]=1)(=[O:11])=[O:10].[N:33]([Si](C)(C)C)=[N+:34]=[N-:35].C([Sn](=O)CCCC)CCC.Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:14]=[C:15]([Cl:32])[C:16]([S:20][C:21]2[S:22][C:23]3[CH:29]=[CH:28][C:27]([C:30]4[NH:35][N:34]=[N:33][N:31]=4)=[CH:26][C:24]=3[N:25]=2)=[C:17]([Cl:19])[CH:18]=1)(=[O:11])=[O:10]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2,4-dichloro-N-[3,5-dichloro-4-(5-cyano -benzothiazol-2-ylsulfanyl)-phenyl]-benzenesulfonamide (297) (250 mg, 0.45 mmol) in toluene (5 mL), was added azidotrimethylsilane (Aldrich, 0.12 mL, 0.90 mmol) and dibutyltin oxide (Aldrich, 11 mg, 0.045 mmol). The resulting mixture was heated at 90° C. overnight (15 hours). A 1M aqueous solution of HCl (50 mL) and ice 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 (20% EtOAc in CH2Cl2, then 10% MeOH in CH2Cl2) to yield 209 mg (77%) of product as a white solid.

Workup

customthe crude reaction mixture
extractionwas extracted 3× with EtOAc (50 mL)
washwashed twice with a brine solution (100 mL)
dry with materialdried over Na2SO4
concentrationconcentrated under vacuum
customThe crude solid was chromatographed (20% EtOAc in CH2Cl2

Sources & evidence

ORD record: ord-919521d3cabc4c85a6e600bc04cdadb7
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968567B2

Reaction notes

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