Methanol → 3-[(Dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoic Acid

HRID 14289

Reaction equation

HRID 14289 reaction equation
[CH2:1]([N:4]([CH2:22][CH2:23][CH3:24])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[CH:16]=1)[C:10]([O:12]C)=[O:11])=[O:6])[CH2:2][CH3:3].CO.O.O.[OH-].[Li+]>C1COCC1>[CH2:22]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[CH:16]=1)[C:10]([OH:12])=[O:11])=[O:6])[CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 21086169Methyl 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoate

Product 1

HCID 210857833-[(Dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoic AcidYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoate (4.5 g) was dissolved in THF (20 mL), methanol (20 mL), and water (20 mL). Lithium hydroxide monohydrate (1.1 g) was added and the mixture was stirred at room temperature for 1.5 h, at which time the organic solvents were removed under reduced pressure. Some ethyl acetate and water were added and the pH was adjusted to about 0 with aq. HCl. The mixture was extracted with ethyl acetate and the organic layers were washed with brine, dried (magnesium sulfate), and concentrated to give 3.8 g of 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoic acid

Workup

  1. customwere removed under reduced pressure
  2. additionSome ethyl acetate and water were added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layers were washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3719294c59ce489dae30df5d7e52577e
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

Loading…