Water → HCID 178484781, compound

HRID 1656360

Reaction equation

HRID 1656360 reaction equation
[Cl:1][C:2]1[C:3]([C:20]#[N:21])=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:5](CCl)[C:6]=1[C:7]([F:10])([F:9])[F:8].[CH3:22][N:23]([CH3:27])[C:24](=[S:26])[SH:25].[Na].O.[CH3:30]N(C)C=O>CCCCCC>[Cl:1][C:2]1[C:3]([C:20]#[N:21])=[C:4]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[N:5]([SH:26]([CH3:30])[C:24](=[S:25])[N:23]([CH3:27])[CH3:22])[C:6]=1[C:7]([F:8])([F:10])[F:9]

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6599Dimethyldithiocarbamic acidHCID 5360545SodiumHCID 110356014-Chloro-1-(chloromethyl)-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile

Product 1

HCID 178484781HCID 178484781, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 4-chloro-1-(chloromethyl)-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (0.7 g, 0.002 mol) and dimethyldithiocarbamic acid, sodium salt (0.57 g, 0.004 mol) in dimethyl formamide is heated at 50°-55° for 30 minutes, cooled to room temperature and poured into water. The resultant mixture is extracted with ethyl acetate. The combined extracts are washed with a saturated sodium chloride solution, dried (MgSO4) and concentrated in vacuo to give an orange oil residue. The residue is mixed with hot hexane, cooled and filtered to give an orange solid filtercake. Recrystallization of the solid from isopropanol gives the title product as a tan crystaline solid, 0.7 g (80% yield), mp 129°-131° C.

Workup

  1. temperatureis heated at 50°-55° for 30 minutes
  2. extractionThe resultant mixture is extracted with ethyl acetate
  3. washThe combined extracts are washed with a saturated sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give an orange oil residue
  7. temperaturecooled
  8. filtrationfiltered
  9. customto give an orange solid filtercake
  10. customRecrystallization of the solid from isopropanol

Sources & evidence

ORD record
ord-c5fdfce118534de088564974051c350e
Source dataset
uspto-grants-1993_10
Patent number
US05254559

Linked notes

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