Hydrochloric Acid → 1-(4-chloro-2-fluoro-5-bis(methanesulphonyl) amino-phenyl)-4,5-dicyano-3-difluoromethyl-1,3-dihydro-2H-imidazol-2-one

HRID 465698Notes

Reaction equation

HRID 465698 reaction equation
ClC1C(OCC#C)=CC(N2C(C#N)=C(C#N)N(CCC)C2=O)=C(F)C=1.[Cl:26][C:27]1[C:32]([N+:33]([O-])=O)=[CH:31][C:30]([N:36]2[C:40]([C:41]#[N:42])=[C:39]([C:43]#[N:44])[N:38]([CH:45]([F:47])[F:46])[C:37]2=[O:48])=[C:29]([F:49])[CH:28]=1.C(N(CC)CC)C.[CH3:57][S:58](Cl)(=[O:60])=[O:59].Cl>ClCCl>[Cl:26][C:27]1[C:32]([N:33]([S:58]([CH3:57])(=[O:60])=[O:59])[S:58]([CH3:57])(=[O:60])=[O:59])=[CH:31][C:30]([N:36]2[C:40]([C:41]#[N:42])=[C:39]([C:43]#[N:44])[N:38]([CH:45]([F:47])[F:46])[C:37]2=[O:48])=[C:29]([F:49])[CH:28]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 198752181-(4-chloro-2-fluoro-5-nitrophenyl)-4,5-dicyano-3-difluoromethyl-1,3-dihydro-2H-imidazol-2-oneHCID 198752701-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4,5-dicyano-3-propyl-1,3-dihydro-2H-imidazol-2-one

Product 1

HCID 198752811-(4-chloro-2-fluoro-5-bis(methanesulphonyl) amino-phenyl)-4,5-dicyano-3-difluoromethyl-1,3-dihydro-2H-imidazol-2-oneYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 77, 1-(4-chloro-2-fluoro-5-nitrophenyl)-4,5-dicyano-3-difluoromethyl-1,3-dihydro-2H-imidazol-2-one, (0.7 g, 2.1 mmol) was dissolved in dichloromethane and treated sequentially at 0° C. with triethylamine (0.56 g, 5.5 mmol) and methanesulphonyl chloride (0.56 g, 5 mmol). The solution was allowed to stir 16 hours at ambient temperature, then poured onto 10 mL of 1N hydrochloric acid solution. The organic layer was separated, washed with brine, and dried and concentrated via standard techniques to furnish 1 g of 1-(4-chloro-2-fluoro-5-bis(methanesulphonyl) amino-phenyl)-4,5-dicyano-3-difluoromethyl-1,3 -dihydro-2H-imidazol-2-one (VI) (M.S. M+ 483).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated via standard techniques

Sources & evidence

ORD record
ord-a95ed1e6de924456859c502025acdcec
Source dataset
uspto-grants-1992_10
Patent number
US05153316

Reaction notes

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