Hydrochloric Acid → HCID 21841974, compound

HRID 1737202Notes

Reaction equation

HRID 1737202 reaction equation
Cl.C([Cl:5])(=O)C.C([NH:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([O:26][CH3:27])=[O:25])(=O)C1C=CC=CC=1>CO>[ClH:5].[NH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([O:26][CH3:27])=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 21841992HCID 21841992, compound

Product 1

HCID 21841974HCID 21841974, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of HCl in methanol (prepared by adding 20 mL of acetyl chloride slowly to 200 mL of methanol) was added the title compound of Step B (31.5 g). The mixture was heated to 60° C. for 1.5 h. The solvent was removed in vacuo. The residue was taken up in 100 mL of diethyl ether and stirred at room temperature for 30 minutes. The ether was decanted off and the solid was taken up in 100 mL of tetrahydrofuran and heated to about 50° C. The mixture was then cooled in an ice water bath and the solid was collected by filtration to provide 11.5 g (47% yield) of the title compound of Step C as a white solid melting at 169-170° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe ether was decanted off
  3. temperatureheated to about 50° C
  4. temperatureThe mixture was then cooled in an ice water bath
  5. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-d9ea65b14e65485e8ebbeb3f4e1c7085
Source dataset
uspto-grants-1999_10
Patent number
US05962436

Reaction notes

Loading…