Hydrochloric Acid → HCID 178527544, compound
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
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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-18646746e3d94d1882300e05cf407ff9
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06770648B2
Reaction notes
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