Benzoyl chloride → HCID 13406007, compound

HRID 1179668Notes

Reaction equation

HRID 1179668 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C(N(C(C)C)C(C)C)C.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCCCCCC>ClCCl>[CH3:9][O:8][C:5]1[N:6]=[CH:7][C:2]([NH:1][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8900HeptaneHCID 811216-Methoxy-3-pyridinylamineHCID 81531Diisopropylethylamine

Product 1

HCID 13406007HCID 13406007, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-amino-2-methoxypyridine (2.48 g, 20.0 mmol) and N-ethyldiisopropylamine (2.84 g, 22.0 mmol) in dichloromethane (20 ml) was cooled in an ice-bath. Benzoyl chloride (3.09 g, 22 mmol) was slowly added by means of a syringe. The cooling bath was removed and stirring was continued at room temperature for 18 hours. Dichloromethane was added and the solution was extracted with water. The organic layer was dried over sodium sulphate, filtered and evaporated in vacuo leaving a dark solid. Crystallisation from ethyl acetate:heptane yielded the title compound (3.44 g, 75% yield).

Workup

  1. customThe cooling bath was removed
  2. additionDichloromethane was added
  3. extractionthe solution was extracted with water
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customleaving a dark solid
  8. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-dcf8f02b306b4720978b3a3744336821
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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