Toluene → HCID 14152465, compound

HRID 1904558Notes

Reaction equation

HRID 1904558 reaction equation
[CH3:1][CH:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][N:13]=3)=[CH:10][C:5]=2[O:4][CH2:3]1.[CH3:19][N:20]([CH3:24])[C:21](Cl)=[O:22].C1(C)C=CC=CC=1.C(N(CC)C(Cl)=O)C>N1C=CC=CC=1.C(OCC)(=O)C.O>[CH3:19][N:20]([CH3:24])[C:21]([NH:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:9]2[CH:8]=[CH:7][C:6]3[CH:2]([CH3:1])[CH2:3][O:4][C:5]=3[CH:10]=2)=[N:13][CH:14]=1)=[O:22]

Participants

8

Reactant 4

HCID 1140Toluene2×HCID 6598Dimethylcarbamoyl ChlorideHCID 6916Diethylcarbamoyl chlorideHCID 14152464HCID 14152464, compound

Product 1

HCID 14152465HCID 14152465, compoundYield 97.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(3-Methyl-2,3-dihydro-6-benzofuryloxy)-5-aminopyridine (0.5 g) was dissolved in 2.5 ml of pyridine, and a solution of composed 0.27 g of dimethylcarbamoyl chloride and 2.5 ml of toluene was added. A solution composed of 0.27 g of diethylcarbamoyl chloride and 2.5 ml of toluene was added, and the mixture was stirred at room temperature for 9 hours. Water and ethyl acetate were added to the reaction mixture, and the organic layer was separated. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. Ethyl acetate was evaporated under reduced pressure, and the precipitated crystals were washed with n-hexane to give 0.63 g (yield 96%) of the desired product as pale brown crystals.

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEthyl acetate was evaporated under reduced pressure
  6. washthe precipitated crystals were washed with n-hexane

Sources & evidence

ORD record
ord-6cfe61f52188497bbf86482051b5da68
Source dataset
uspto-grants-1989_06
Patent number
US04838924

Reaction notes

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