Thionyl Chloride → HCID 19047168, compound

HRID 275435Notes

Reaction equation

HRID 275435 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-0151c582293b4fad9d951157a81a902f
Source dataset
uspto-grants-1995_02
Patent number
US05393735

Reaction notes

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