Thionyl Chloride → HCID 19047168, compound

HRID 1441092Notes

Reaction equation

HRID 1441092 reaction equation
[C:1]([C:4]1[C:5]([Cl:23])=[CH:6][C:7]([F:22])=[C:8]([N:10]2[C:15](=[O:16])[CH2:14][CH:13]([C:17]([F:20])([F:19])[F:18])[CH2:12][C:11]2=[O:21])[CH:9]=1)([OH:3])=O.S(Cl)([Cl:26])=O>CN(C)C=O.C1(C)C=CC=CC=1>[Cl:26][C:1]([C:4]1[C:5]([Cl:23])=[CH:6][C:7]([F:22])=[C:8]([N:10]2[C:15](=[O:16])[CH2:14][CH:13]([C:17]([F:18])([F:20])[F:19])[CH2:12][C:11]2=[O:21])[CH:9]=1)=[O:3]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 19047100HCID 19047100, compound2×

Product 1

HCID 19047168HCID 19047168, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of N-(5'-carboxy-4'-chloro-2'-fluorophenyl)-3-(trifluoromethyl)glutarimide (Compound 62) (3.0 g, 8.5 mmol) and 35 ml toluene was added thionyl chloride (0.80 ml, 1.3 g, 1.1 mmol) followed by 2 drops of N,N-dimethylformamide and the suspension was heated to 90° C. for two hours. The resulting clear, orange solution was cooled to room temperature and the solvents were removed in vacuo (1 mm Hg). The resulting N-(5'-chlorocarbonyl-4'-chloro-2'-fluorophenyl)-3-(trifluoromethyl)glutarimide, a dark semisolid, could be used without further purification.

Workup

  1. temperatureThe resulting clear, orange solution was cooled to room temperature
  2. customthe solvents were removed in vacuo (1 mm Hg)
  3. customThe resulting N-(5'-chlorocarbonyl-4'-chloro-2'-fluorophenyl)-3-(trifluoromethyl)glutarimide, a dark semisolid, could be used without further purification

Sources & evidence

ORD record
ord-a00d7bc85db7438492ba189c13e0e980
Source dataset
uspto-grants-1996_03
Patent number
US05502027

Reaction notes

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