Pyridine → 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4,5-dicyano-3-propyl-1,3-dihydro-2H-imidazol-2-one

HRID 465692Notes

Reaction equation

HRID 465692 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:13]([C:14]#[N:15])=[C:12]([C:16]#[N:17])[N:11]([CH3:18])[C:10]2=[O:19])=[C:4]([F:20])[CH:3]=1.C(O[C:25](=O)[CH3:26])(=O)C.N1C=C[CH:31]=[CH:30][CH:29]=1>>[Cl:1][C:2]1[C:7]([O:8][CH2:31][C:30]#[CH:29])=[CH:6][C:5]([N:9]2[C:13]([C:14]#[N:15])=[C:12]([C:16]#[N:17])[N:11]([CH2:18][CH2:25][CH3:26])[C:10]2=[O:19])=[C:4]([F:20])[CH:3]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 198751891-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-one3×

Product 1

HCID 198752701-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4,5-dicyano-3-propyl-1,3-dihydro-2H-imidazol-2-one

Procedure

The product of Example 32, 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-one, (VIII) (200 mg, 0.68 mmol) was stirred in 10 mL pyridine at room temperature. To this mixture was added acetic anhydride (100 mg, 0.98 mmol). After stirring for 10 minutes the mixture was poured over a mixture of ice/HCl and filtered. Recrystallization from ethyl acetate/heptane gave 60 mg of 1-(4-chloro-2-fluoro-5-acetoxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-one (VI) (m.p. 164°-6° C.).

Workup

  1. filtrationfiltered
  2. customRecrystallization from ethyl acetate/heptane

Sources & evidence

ORD record
ord-00c58af717ab49f6961ef8dbde047771
Source dataset
uspto-grants-1992_10
Patent number
US05153316

Reaction notes

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