Sodium Chloride → 4-Methoxyphenyl-1-[5-isopropyl-2,4-bis(methoxymethoxy)-benzoyl]thiosemicarbazide

HRID 1947184Notes

Reaction equation

HRID 1947184 reaction equation
[CH:1]([C:4]1[C:5]([O:17][CH2:18][O:19][CH3:20])=[CH:6][C:7]([O:13][CH2:14][O:15][CH3:16])=[C:8]([CH:12]=1)[C:9]([OH:11])=O)([CH3:3])[CH3:2].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][NH:30][C:31]([NH2:33])=[S:32])=[CH:25][CH:24]=1.O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[Cl-].[Na+]>CN(C)C=O>[CH3:21][O:22][C:23]1[CH:24]=[CH:25][C:26]([N:29]([C:9](=[O:11])[C:8]2[CH:12]=[C:4]([CH:1]([CH3:2])[CH3:3])[C:5]([O:17][CH2:18][O:19][CH3:20])=[CH:6][C:7]=2[O:13][CH2:14][O:15][CH3:16])[NH:30][C:31]([NH2:33])=[S:32])=[CH:27][CH:28]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 28261724-MethoxyphenylthiosemicarbazideHCID 58236465HCID 58236465, compound

Product 1

HCID 866243104-Methoxyphenyl-1-[5-isopropyl-2,4-bis(methoxymethoxy)-benzoyl]thiosemicarbazideYield 86.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

5-isopropyl-2,4-bis(methoxymethoxy)-benzoic acid (IM3-a: 16.4 g, 54.5 mmol), 4-methoxyphenylthiosemicarbazide (F53-02: 11.3 g, 57.3 mmol), dimethylformamide (150 mL) and 1-hydroxybenzotriazole monohydrate (8.11 g, 60.0 mmol) were placed in a 500 mL eggplant shaped flask. The reaction mixture was cooled to 0° C. and mixed with a suspension of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (11.5 g, 60 mmol) in dimethylformamide (100 mL). The mixture was stirred for 4 hours and allowed to come to room temperature. After completing the reaction, saturated sodium chloride solution (500 mL) was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate (500 mL). The organic layer thus obtained was washed 4 times with saturated sodium chloride solution (500 mL) and dried over anhydrous sodium sulfate. After removing sodium sulfate by filtration, the solvent was distilled under reduced pressure, and the solids obtained were suspended in hexane (1000 mL) for purification and collected by filtration. The solids thus obtained were dried under reduced pressure to obtain the title compound (F53-03: 21.9 g, 83.8%).

Workup

  1. customto come to room temperature
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was extracted twice with ethyl acetate (500 mL)
  4. customThe organic layer thus obtained
  5. washwas washed 4 times with saturated sodium chloride solution (500 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removing sodium sulfate
  8. filtrationby filtration
  9. distillationthe solvent was distilled under reduced pressure
  10. customthe solids obtained
  11. customwere suspended in hexane (1000 mL) for purification
  12. filtrationcollected by filtration
  13. customThe solids thus obtained
  14. customwere dried under reduced pressure

Sources & evidence

ORD record
ord-3160f81211b746b295615af0cac7dbfb
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

Loading…