Pyridine → HCID 131727933, compound

HRID 2243213Notes

Reaction equation

HRID 2243213 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:10]=[C:11]([C:15]3([C:21]#[N:22])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:31]>ClCCCl>[C:33]1([O:32][C:30](=[O:31])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([S:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]4([C:21]#[N:22])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[CH:10]=3)=[CH:4][CH:3]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 11232153HCID 11232153, compound

Product 1

HCID 131727933HCID 131727933, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-{3-[(4-aminophenyl)thio]phenyl}tetrahydro-2H-pyran-4-carbonitrile (2.50 g, 8.06 mmol) (example 4) in 1,2-dichloroethane (20 mL) and pyridine (0.95 g, 12.097 mmol) was cooled to 0° C. Phenyl chloroformate (1.89 g, 12.097 mmol) was added dropwise to the reaction mixture at 0° C. The reaction mixture was stirred at room temperature for about 1 hour. The solvent was evaporated under vacuum, toluene was added to remove traces of pyridine, then hexane was added and the solid so obtained was filtered and dried. Yield:4.30 g.

Workup

  1. customThe solvent was evaporated under vacuum, toluene
  2. additionwas added
  3. customto remove traces of pyridine
  4. additionhexane was added
  5. customthe solid so obtained
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-ffb3a9043b514d519a510f69a58f5868
Source dataset
uspto-grants-2010_03
Patent number
US07674811B2

Reaction notes

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