Propargyl bromide → 5-(3-Chloro-5-trifluoromethylpyridin-2-yl)-1-(1-methylethyl)-3-(2-propynyl)benzimidazol-2-one

HRID 1276082Notes

Reaction equation

HRID 1276082 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:25]=[CH:24][C:15]3[N:16]([CH:21]([CH3:23])[CH3:22])[C:17](=[O:20])[N:18]([CH3:19])[C:14]=3[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Cl[C:27]1C(C2C=CC3N(C(C)C)C(=O)NC=3C=2)=NC=C(C(F)(F)F)[CH:32]=1.C(Br)C#C>>[Cl:1][C:2]1[C:3]([C:12]2[CH:25]=[CH:24][C:15]3[N:16]([CH:21]([CH3:22])[CH3:23])[C:17](=[O:20])[N:18]([CH2:19][C:27]#[CH:32])[C:14]=3[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1

Participants

4

Reactant 3

HCID 7842Propargyl bromideHCID 221148405-(3-Chloro-5-trifluoromethylpyridin-2-yl)-3-methyl-1-(1-methylethyl)benzimidazol-2-oneHCID 221148555-(3-Chloro-5-trifluoromethylpyridin-2yl)-1-(1-methylethyl)benzimidazol-2-one

Product 1

HCID 221148655-(3-Chloro-5-trifluoromethylpyridin-2-yl)-1-(1-methylethyl)-3-(2-propynyl)benzimidazol-2-oneYield 47%

Procedure

In a similar manner to the preparation of 5-(3-chloro-5-trifluoromethylpyridin-2yl)-3-methyl-1-(1-methylethyl)benzimidazol-2-one described above, 2.5 g of 5-(3-chloro-5-trifluoromethylpyridin-2yl)-1-(1-methylethyl)benzimidazol-2-one and 0.9 g of propargyl bromide gave, after chromatography on silica gel, 1.3 g (47%) of colorless crystals. Yield: 47%; m.p.: 109-111° C.

Workup

  1. customgave

Sources & evidence

ORD record
ord-d044a7ba606c4b2fa8146958bc4c8915
Source dataset
uspto-grants-2000_12
Patent number
US06165941

Reaction notes

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