Benzoyl chloride → HCID 18700007, compound

HRID 2288615Notes

Reaction equation

HRID 2288615 reaction equation
[C:1]([Cl:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[O:15][C:14]([C:16]2[S:20][C:19]([CH2:21][N:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)=[N:13][N:12]=1>N1C=CC=CC=1>[ClH:9].[N:22]1([CH2:21][C:19]2[S:20][C:16]([C:14]3[O:15][C:11]([NH:10][C:1](=[O:8])[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[N:12][N:13]=3)=[CH:17][CH:18]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 18699937HCID 18699937, compound

Product 1

HCID 18700007HCID 18700007, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

1.8 ml (15.0 mmol) of benzoyl chloride was added to 15 ml of pyridine solution containing 278 mg (1.0 mmol) of the compound of Example 43, and the mixture was stirred at 80° C. for 10 days. The reaction solution was concentrated under a reduced pressure, chloroform was added to the resulting residue, followed by washing with water and drying over anhydrous magnesium sulfate. The solvent was evaporated, the resulting residue was purified by a silica gel column chromatography. Then, the resulting crude crystals were recrystallized from ethanol-diisopropyl ether to give 241 mg of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under a reduced pressure, chloroform
  2. additionwas added to the resulting residue
  3. washby washing with water
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe resulting residue was purified by a silica gel column chromatography
  7. customThen, the resulting crude crystals were recrystallized from ethanol-diisopropyl ether

Sources & evidence

ORD record
ord-d9986c1c58074a428f8f42c2e6dd893c
Source dataset
uspto-grants-2000_07
Patent number
US06090804

Reaction notes

Loading…