4-Aminobiphenyl → HCID 24995122, compound

HRID 1258623Notes

Reaction equation

HRID 1258623 reaction equation
[C:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([S:24](Cl)(=[O:26])=[O:25])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]>N1C=CC=CC=1>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([S:24]([NH:7][C:4]2[CH:3]=[CH:2][C:1]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][CH:5]=2)(=[O:25])=[O:26])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]

Participants

4

Reactant 2

HCID 71024-AminobiphenylHCID 27341833,4-Dimethoxybenzenesulfonyl chloride

Product 1

HCID 24995122HCID 24995122, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of biphenyl-4-amine (338 mg, 2 mmol) in 10 mL of dry pyridine followed by 529 mg of 3,4-dimethoxybenzenesulfonyl chloride. The solution was stirred at room temperature under Argon. After 21 h, the pyridine was removed in vacuo and flashed off with toluene. The residue was partitioned between EtOAc and 1M NaOH. The organic phase was washed with 1M NaOH until no turbidity was observed on rectification of a small sample. The alkaline phase was made acidic (˜pH 3) with 1M HCl and extracted with EtOAc. After drying over Na2SO4, solvent was removed in vacuo. The crude product (0.79 g) was obtained as a glass which slowly crystallized. Addition of hexane caused complete solidification. The solid was taken up in EtOAc (11 mL), diluted with hexane (11 mL) and seeded to give 534 mg of white needles. The product had mp 171-173° C.

Workup

  1. customthe pyridine was removed in vacuo
  2. customThe residue was partitioned between EtOAc and 1M NaOH
  3. washThe organic phase was washed with 1M NaOH until no turbidity
  4. extractionextracted with EtOAc
  5. dry with materialAfter drying over Na2SO4, solvent
  6. customwas removed in vacuo
  7. customThe crude product (0.79 g) was obtained as a glass which
  8. customslowly crystallized
  9. additionAddition of hexane caused complete solidification
  10. additiondiluted with hexane (11 mL)

Sources & evidence

ORD record
ord-261d9090324643e79f7ff814ecbb266f
Source dataset
uspto-grants-2013_06
Patent number
US08466182B2

Reaction notes

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