Water → HCID 61182641, compound

HRID 2092522Notes

Reaction equation

HRID 2092522 reaction equation
C([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[F:22])=[O:13])=[CH:7][CH:6]=1)C.O.[OH-].[Li+].O>CCO.C1COCC1>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:12](=[O:13])[NH:11][C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:23])=[O:3])=[CH:6][CH:7]=2)=[C:16]([F:22])[CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 25236836HCID 25236836, compound

Product 1

HCID 61182641HCID 61182641, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[3-(4-bromo-2-fluoro-phenyl)-ureido]-benzoic acid ethyl ester (0.7 g, 0.0018 mol) in EtOH (5 mL) and THF (4 mL), was added a solution of lithium hydroxide monohydrate in water (0.385 g, 0.009 mol, in 5 mL water) at room temperature. The reaction mass was stirred at room temperature for 5 h. The volatiles were evaporated under reduced pressure. The white solid was washed with diethyl ether. Subsequently, the reaction mixture was acidified with 2 N HCl [pH-6] at 0° C. to afford the solid compound. The solid material was collected by filtration and dried to obtain the title compound [0.55 g, 84%]; LC-MS (ESI): Calculated mass: 352.0; Observed mass: 352.9 [M+H]+ (RT: 1.49 min).

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. washThe white solid was washed with diethyl ether
  3. customwas acidified with 2 N HCl [pH-6] at 0° C.
  4. customto afford the solid compound
  5. filtrationThe solid material was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-d0c303ba243b42aaa5d715f7bb4064b8
Source dataset
uspto-grants-2013_05
Patent number
US08440662B2

Reaction notes

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