Methanol → HCID 68784637, compound

HRID 80069Notes

Reaction equation

HRID 80069 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:25])[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:16][CH2:15][N:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:22]=3[CH3:23])[C:13]2=[O:24])=[CH:8][CH:7]=1.O.CO>C1COCC1.C(Cl)Cl>[CH3:23][C:22]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N:14]1[CH2:15][CH2:16][N:12]([C:9]2[CH:10]=[CH:11][C:6]([C:5]([OH:25])=[O:4])=[CH:7][CH:8]=2)[C:13]1=[O:24]

Participants

7

Reactant 4

HCID 887Methanol2×HCID 962WaterHCID 3939Lithium HydroxideHCID 68789034HCID 68789034, compound

Product 1

HCID 68784637HCID 68784637, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (46.4 mg, 3.782 mmol) was added to a stirred solution of 4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzoic acid methyl ester (230 mg, 0.7387 mmol) in (3:2:1) THF (10 mL, water (6 mL) and MeOH (3 mL). The reaction mixture was stirred at room temperature for 4 hours. The reaction was monitored by TLC (10% MeOH in DCM). The reaction mixture was concentrated under reduced pressure, followed by the addition of ice water and neutralized with 1N HCl till a pH of about 2 was attained. The precipitate was collected and dried under reduced pressure to afford 210 mg of 4-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzoic acid (95% yield).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionfollowed by the addition of ice water and neutralized with 1N HCl till a pH of about 2
  3. customThe precipitate was collected
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-0ad1d91dc182426fa6916e76e6c51298
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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