Phosphorus oxychloride → HCID 16778897, compound

HRID 334517Notes

Reaction equation

HRID 334517 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[C:5]([NH:7][NH:8][C:9](=[O:12])[CH2:10][Cl:11])=O.P(Cl)(Cl)(Cl)=O>C(#N)C>[Cl:11][CH2:10][C:9]1[O:12][C:5]([C:4]2[CH:3]=[C:2]([Cl:1])[CH:15]=[C:14]([Cl:16])[CH:13]=2)=[N:7][N:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 13365860HCID 13365860, compound

Product 1

HCID 16778897HCID 16778897, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3,5-dichlorobenzohydrazide 5 (0.5 g, 2.4 mmol) and K2CO3 (0.61 g, 4.4 mmol) in acetonitrile (30 mL) was added 2-chloroacetyl chloride (0.41 g, 3.66 mmol) dropwise at ambient temperature. The resulting mixture was stirred at ambient temperature for 16 hours. The solid was collected, washed with H2O and ether, and dried to afford 3,5-dichloro-N′-(2-chloroacetyl)benzohydrazide 6 (0.63 g, 92%) which was used for the next step without further purification. A mixture of 3,5-dichloro-N′-(2-chloroacetyl)benzohydrazide 6 (0.63 g, 2.24 mmol) and phosphorous oxychloride (0.51 g, 3.36 mmol) in acetonitrile (20 mL) was stirred under reflux for 16 hours and concentrated. The residue was subjected to flush column chromatography eluting with 10-25% acetone/hexanes to give compound 7 (0.52 g). Yield: 88%.

Workup

  1. customwas used for the next step without further purification
  2. temperatureunder reflux for 16 hours
  3. concentrationconcentrated
  4. customto flush column chromatography
  5. washeluting with 10-25% acetone/hexanes

Sources & evidence

ORD record
ord-7136fa2362854a15b85529efc6d46b77
Source dataset
uspto-grants-2014_11
Patent number
US08883827B2

Reaction notes

Loading…