Hydrochloric Acid → HCID 22142147, compound

HRID 1824696Notes

Reaction equation

HRID 1824696 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([NH:20][NH2:21])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1.N1C=CC=CC=1.[C:28](Cl)(=[O:30])[CH3:29].Cl>C(OCC)(=O)C.O>[F:2][C:3]1[CH:4]=[C:5]([NH:20][NH:21][C:28](=[O:30])[CH3:29])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 22142154HCID 22142154, compound

Product 1

HCID 22142147HCID 22142147, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To [3-fluoro-4-[3-(trifluoromethyl)phenoxy]phenyl]hydrazine hydrochloride (0.35 g) prepared using the method described in Example 1, in ethyl acetate (5 mL), was added pyridine (0.24 mL) at −10° C. After dropwise addition of acetyl chloride (0.1 mL), the mixture was stirred for 3 h and then acidified with 6 M HCl. Water was added, and the product was extracted with ether. The organic layer was separated, dried, and concentrated. The residue was purified by column chromatography on silica (using dichloromethane, followed by 5:1 dichloromethane:ether as eluants) to give a solid (0.2 g).

Workup

  1. extractionthe product was extracted with ether
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica (using dichloromethane, followed by 5:1 dichloromethane:ether as eluants)

Sources & evidence

ORD record
ord-8d75ea7c051b451ca8495733475d3360
Source dataset
uspto-grants-2006_05
Patent number
US07045512B2

Reaction notes

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