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

HRID 349078Notes

Reaction equation

HRID 349078 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-7404385beab948f6a60ceb5197973960
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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