1,1'-Carbonyldiimidazole → 5-(3-Chloro-5-trifluoromethylpyridin-2yl)-1-(1-methylethyl)benzimidazol-2-one

HRID 1276080Notes

Reaction equation

HRID 1276080 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[NH:8][CH:9]([CH3:11])[CH3:10].[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>O1CCCC1>[Cl:18][C:17]1[C:12]([C:4]2[CH:5]=[CH:6][C:7]3[N:8]([CH:9]([CH3:11])[CH3:10])[C:23](=[O:24])[NH:1][C:2]=3[CH:3]=2)=[N:13][CH:14]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:16]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 221148412-[3-Amino-4-(1-methylethylamino)phenyl]-3-chloro-5-trifluoromethylpyridine

Product 1

HCID 221148555-(3-Chloro-5-trifluoromethylpyridin-2yl)-1-(1-methylethyl)benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

37.4 g of 2-[3-amino-4-(1-methylethylamino)-phenyl]-3-chloro-5-trifluoromethylpyridine and 27.6 g of carbonyldiimidazole were heated at reflux temperature for four hours in 200 ml of anhydrous tetrahydrofuran, after which the reaction mixture was concentrated. The residue was treated with 100 ml of 10% strength hydrochloric acid and the mixture was extracted three times with 100 ml of methylene chloride each time. The combined organic phases were washed twice with 50 ml of water each time, dried over sodium sulfate and concentrated. The crude product was stirred with ether, then separated off and dried. Yield: 29.8 g (74%) of colorless crystals; m.p.: 192-193° C.

Workup

  1. concentrationafter which the reaction mixture was concentrated
  2. additionThe residue was treated with 100 ml of 10% strength hydrochloric acid
  3. extractionthe mixture was extracted three times with 100 ml of methylene chloride each time
  4. washThe combined organic phases were washed twice with 50 ml of water each time
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customseparated off
  8. customdried

Sources & evidence

ORD record
ord-fcbd50f855634501b22f85f1e5f56efc
Source dataset
uspto-grants-2000_12
Patent number
US06165941

Reaction notes

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