Benzoyl chloride → HCID 22401682, compound

HRID 260508Notes

Reaction equation

HRID 260508 reaction equation
[NH2:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]3[CH2:12][CH2:13][S:14][C:7]3=[N:6][C:5]=2[N:4]([CH3:15])[N:3]=1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[C:16]([NH:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]3[CH2:12][CH2:13][S:14][C:7]3=[N:6][C:5]=2[N:4]([CH3:15])[N:3]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 22401692HCID 22401692, compound

Product 1

HCID 22401682HCID 22401682, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

In 14 ml of pyridine was dissolved 1.40 g (6.27 mmol) of Compound 13 prepared in Example 10, and 0.80 ml (6.9 mmol) of benzoyl chloride was added to the solution, followed by stirring at 50° C. for 30 minutes. After evaporation of the solvent, the residue was subjected to partition between chloroform and water. The chloroform layer was washed with a dilute aqueous solution of hydrochloric acid and water, and concentrated to dryness under reduced pressure. The residue was recrystallized from chloroform/ethanol to give 1.81 g (80%) of Compound 21 in pure form.

Workup

  1. additionwas added to the solution
  2. customAfter evaporation of the solvent
  3. customto partition between chloroform and water
  4. washThe chloroform layer was washed with a dilute aqueous solution of hydrochloric acid and water
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue was recrystallized from chloroform/ethanol

Sources & evidence

ORD record
ord-2bafd79a10d646e89bea6d90c93642d2
Source dataset
uspto-grants-1996_06
Patent number
US05527908

Reaction notes

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