4-Toluenesulfonyl chloride → HCID 2794024, compound

HRID 600613Notes

Reaction equation

HRID 600613 reaction equation
[C:1]1([C:12]2[C:13]([NH2:22])=[CH:14][CH:15]=[C:16]3[C:21]=2[CH:20]=[CH:19][CH:18]=[CH:17]3)[C:2]([NH2:11])=[CH:3][CH:4]=[C:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[CH:6]2.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>N1C=CC=CC=1.C(OCC)(=O)C>[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([NH:22][C:13]2[C:12]([C:1]3[C:2]([NH:11][S:29]([C:26]4[CH:27]=[CH:28][C:23]([CH3:33])=[CH:24][CH:25]=4)(=[O:31])=[O:30])=[CH:3][CH:4]=[C:5]4[C:10]=3[CH:9]=[CH:8][CH:7]=[CH:6]4)=[C:21]3[C:16](=[CH:15][CH:14]=2)[CH:17]=[CH:18][CH:19]=[CH:20]3)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 205712,2'-Diamino-1,1'-dinaphthyl

Product 1

HCID 2794024HCID 2794024, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under nitrogen atmosphere, to a solution in which 1,1′-binaphthyl-2,2′-diamine (0.5 mmol) was dissolved in pyridine (1 mL) was added p-toluenesulfonyl chloride (1.1 mmol) at room temperature, and the mixture was reacted for 5 to 12 hours with stirring. After completion of the reaction, the resulting red suspension was diluted with ethyl acetate, and back-extracted with 1N hydrochloric acid to remove pyridine. The resulting organic layer was dried with sodium sulfate to remove the solvent, and the residue was purified by column chromatography to obtain an objective substance as a pale yellow to white solid in more than 95% yield.

Workup

  1. customthe mixture was reacted for 5 to 12 hours
  2. customAfter completion of the reaction
  3. extractionback-extracted with 1N hydrochloric acid
  4. customto remove pyridine
  5. dry with materialThe resulting organic layer was dried with sodium sulfate
  6. customto remove the solvent
  7. customthe residue was purified by column chromatography
  8. customto obtain an objective substance as a pale yellow to white solid in more than 95% yield

Sources & evidence

ORD record
ord-69bf4a24b8f64c3a96d88ab3e40cadb9
Source dataset
uspto-grants-2011_03
Patent number
US07902207B2

Reaction notes

Loading…