Hydrazine → HCID 59240015, compound

HRID 1673045Notes

Reaction equation

HRID 1673045 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[C:20]([C:22]([O:24]CC)=O)[N:19]=[C:18]3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]([F:36])([F:35])[F:34])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].O1CCOCC1.[NH2:43][NH2:44]>C1(C)C=CC=CC=1>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:12]=[CH:13][C:14]([N:17]3[CH:21]=[C:20]([C:22]([NH:43][NH2:44])=[O:24])[N:19]=[C:18]3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]([F:35])([F:34])[F:36])=[CH:15][CH:16]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 312751,4-DioxaneHCID 59240098HCID 59240098, compound

Product 1

HCID 59240015HCID 59240015, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl 1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)-phenyl)-1H-imidazole-4-carboxylate (2.63 g, 5.110 mmol) in 8 mL of 1:1 PhMe:Dioxane was added hydrazine (1 mL, 31.86 mmol). The reaction was heated at 90° C. for 12 h and then cooled to room temperature. The reaction was filtered through a small amount of celite to remove a black precipitate and then concentrated and placed on the high vacuum pump. The residue was dissolved in a minimum amount of dichloromethane and slowly added to 200 mL ether with stirring. 100 mL of ether was added and the white precipitate was filtered and rinsed with ether to afford 1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)-phenyl)-1H-imidazole-4-carbohydrazide (1.77 g, 70%) as a white solid. 1H-NMR (DMSO, 400 MHz) δ 9.21 (s, 1H), 8.16 (s, 1H), 8.14-8.13 (m, 1H), 8.03-8.00 (m, 1H), 7.92-7.89 (m, 1H), 7.85-7.89 (m, 3H), 7.74-7.64 (m, 4H), 7.36 (d, J=8.58 Hz, 2H), 4.44 (brs, 2H), 3.28 (s, 3H); MS (ES): 501.3 [M+H]+ and 523.2 [M+Na]+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe reaction was filtered through a small amount of celite
  3. customto remove a black precipitate
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in a minimum amount of dichloromethane
  6. additionslowly added to 200 mL ether
  7. addition100 mL of ether was added
  8. filtrationthe white precipitate was filtered
  9. washrinsed with ether

Sources & evidence

ORD record
ord-57259a00917f4bb99c8feb9900021345
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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