Dichloromethane → Trifluoromethyl 1-chloro-N-(p-chlorobenzyl)thioformimidate

HRID 1464680Notes

Reaction equation

HRID 1464680 reaction equation
[F:1][C:2]([F:6])([F:5])[S:3]Cl.[Cl:7][C:8]1[CH:16]=[CH:15][C:11]([CH2:12][N+:13]#[C-:14])=[CH:10][CH:9]=1.C(Cl)[Cl:18]>>[Cl:18][C:14](=[N:13][CH2:12][C:11]1[CH:15]=[CH:16][C:8]([Cl:7])=[CH:9][CH:10]=1)[S:3][C:2]([F:6])([F:5])[F:1]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 67900Methanesulfenyl chloride, trifluoro-HCID 27574091-Chloro-4-(isocyanomethyl)benzene

Product 1

HCID 18930385Trifluoromethyl 1-chloro-N-(p-chlorobenzyl)thioformimidateYield 68%

Procedure

Trifluoromethylsulfenyl chloride (4.0 g, 0.03 mol) is bubbled over 30 minutes into a solution of 4-chlorobenzylisonitrile (3.0 g, 0.02 mol) in methylene chloride, causing the formation of a white precipitate. The suspension is stirred for 16 hours at room temperature and filtered to remove solids. The white filter cake is washed with methylene chloride and solvent is removed under reduced pressure to obtain an amber oil. Bulb-to-bulb distillation of the oil (90°-100° C., 0.05 mmhg) gives the title product as a colorless oil (3.9 g, 68%).

Workup

  1. filtrationfiltered
  2. customto remove solids
  3. washThe white filter cake is washed with methylene chloride and solvent
  4. customis removed under reduced pressure
  5. customto obtain an amber oil
  6. distillationBulb-to-bulb distillation of the oil (90°-100° C., 0.05 mmhg)

Sources & evidence

ORD record
ord-b2e43a961f6743d3b28e2d4174581de4
Source dataset
uspto-grants-1994_04
Patent number
US05306827

Reaction notes

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