Hydrochloric Acid → HCID 59240086, compound

HRID 1673020Notes

Reaction equation

HRID 1673020 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:28]2[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:35])[N:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:18]=3)=[CH:13][C:12]=2[Cl:27])[CH:10]=1)=[O:5])C.CO.[OH-].[Na+].Cl>CCOC(C)=O>[Cl:27][C:12]1[CH:13]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH3:26])(=[O:24])=[O:25])[CH:18]=2)[CH:15]=[CH:16][C:11]=1[N:9]1[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=[C:8]1[C:28]1[C:29]([Cl:35])=[CH:30][CH:31]=[CH:32][C:33]=1[Cl:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 15947801HCID 15947801, compound

Product 1

HCID 59240086HCID 59240086, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a 250 mL round bottom flask was added 1-(3-Chloro-3′-methanesulfonyl-biphenyl-4-yl)-2-(2,6-dichloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester (4.07 g, 7.40 mmol), MeOH (72 mL), and 2N aq NaOH (18.5 mL). The reaction solution was allowed to stir at 50° C. for 2 hr. The reaction solution was diluted with EtOAc (200 mL), neutralized by the addition of aq 1 N HCl, and poured into a separatory funnel. The organic phase was partitioned, and the aqueous phase was and extracted with EtOAc (150 mL×2). The combined organic phases were dried over Na2SO4, filtered into a round bottom flask and concentrated on the rotavapor. The crude residue was reprecipitated in an EtOAc/hexane solution and the solid precipitate was filtered under vacuum to afford 3.22 g (83% yield) of title product. MS (ESI) 521.3, 523.3, 525.3 [M+H]+.

Workup

  1. additionpoured into a separatory funnel
  2. customThe organic phase was partitioned
  3. extractionextracted with EtOAc (150 mL×2)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered into a round bottom flask
  6. concentrationconcentrated on the rotavapor
  7. customThe crude residue was reprecipitated in an EtOAc/hexane solution
  8. filtrationthe solid precipitate was filtered under vacuum

Sources & evidence

ORD record
ord-c1b27a4464c947fea54b49ab46e92ad7
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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