4-Isopropylbenzoic Acid → HCID 86624588, compound

HRID 2172161Notes

Reaction equation

HRID 2172161 reaction equation
[CH:1]([C:4]1[CH:23]=[CH:22][C:7]([C:8]([NH:10][NH:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].COC(C1C=CC(NN)=CC=1)=O.C(C1C=CC(C(O)=O)=CC=1)(C)C.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:57])=CC=1.[OH-].[Na+]>C1COCC1.CCOCC.C1(C)C=CC=CC=1>[CH:1]([C:4]1[CH:23]=[CH:22][C:7]([C:8]([NH:10][NH:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)=[S:57])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

9

Reactant 5

HCID 108204-Isopropylbenzoic AcidHCID 14798Sodium HydroxideHCID 87949Lawesson's reagentHCID 408928Methyl 4-hydrazinylbenzoateHCID 66616109HCID 66616109, compound

Product 1

HCID 86624588HCID 86624588, compoundYield 83.2%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To a toluene (25 mL) solution of methyl 4-[2-(4-isopropylbenzoyl)hydrazino]benzoate (0.94 g, 3.0 mmol), prepared from 4-methoxycarbonylphenylhydrazine and 4-isopropylbenzoic acid using the coupling technique described above, is added Lawesson's Reagent (1.82 g, 4.5 mmol). The mixture is stirred at 120° C. for 10 hr and cooled to room temperature. The precipitate is removed and the filtrate is concentrated, chromatographed (silica gel, 1:9 ethyl acetate-hexane) to give an intermediate compound, MS (ES+): m/e 496. The intermediate is then treated with NaOH (1.25N, 2.63 mL, 3.3 mmol) in THF (20 mL) at 65° C. for 1 h. The solvent is then replaced with ether (50 mL), and the mixture is washed with water, dried and chromatographed to provide the thiohydrazide, methyl 4-{2-[(4-isopropylphenyl)carbonothioyl]hydrazino}benzoate (0.82 g, 81%). MS (ES+): m/e 329.

Workup

  1. temperaturecooled to room temperature
  2. customThe precipitate is removed
  3. concentrationthe filtrate is concentrated
  4. customchromatographed (silica gel, 1:9 ethyl acetate-hexane)
  5. customto give an intermediate compound, MS (ES+)
  6. washthe mixture is washed with water
  7. customdried
  8. customchromatographed

Sources & evidence

ORD record
ord-a17c88e5f8184908be9b4b036f78076a
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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