Pyridine → 2-(3',5'-Dichlorophenyl)-4,4-dimethyl-5-chloro-5-dichloromethyloxazoline

HRID 1780008

Reaction equation

HRID 1780008 reaction equation
[CH3:1][C:2]([NH:6][C:7](=[O:16])[C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10]([Cl:15])[CH:9]=1)([CH3:5])[C:3]#C.[Cl:17]Cl.N1C=CC=CC=1.[CH2:25]([Cl:27])[Cl:26]>CCOCC>[Cl:15][C:10]1[CH:9]=[C:8]([C:7]2[O:16][C:1]([Cl:17])([CH:25]([Cl:27])[Cl:26])[C:2]([CH3:5])([CH3:3])[N:6]=2)[CH:13]=[C:12]([Cl:14])[CH:11]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 24526ChlorineHCID 32154Propyzamide

Product 1

HCID 544601542-(3',5'-Dichlorophenyl)-4,4-dimethyl-5-chloro-5-dichloromethyloxazoline

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N-(1',1'-dimethylpropynyl)-3,5-dichlorobenzamide (25 gm, 0.096 m) was dissolved in methylene chloride (300 ml) and excess chlorine (2.5-3 equivalents) was bubbled through this solution at room temperature. After the starting material had disappeared (as indicated by thin layer chromatography, TLC), this solution was washed with aqueous sodium sulfite and the solvent was removed. The white solid obtained was slurried in ether (250 ml) and pyridine (8.0 gm) was added. The mixture was stirred for about 1 hour and then filtered to remove solids. The mother liquor was washed sequentially with cold 1% hydrochloric acid (25 ml), sodium bicarbonate (50 ml), water and brine. The solvent was removed after drying over magnesium sulfate and 28 gm of 2-(3',5'-dichlorophenyl)-4,4-dimethyl-5-chloro-5-dichloromethyloxazoline was obtained.

Workup

  1. washthis solution was washed with aqueous sodium sulfite
  2. customthe solvent was removed
  3. customThe white solid obtained
  4. filtrationfiltered
  5. customto remove solids
  6. washThe mother liquor was washed sequentially with cold 1% hydrochloric acid (25 ml), sodium bicarbonate (50 ml), water and brine
  7. customThe solvent was removed
  8. dry with materialafter drying over magnesium sulfate

Sources & evidence

ORD record
ord-b58c25ce04724492a98d2b265a4958f1
Source dataset
uspto-grants-1997_05
Patent number
US05629346

Linked notes

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