Water → Phenyl (3-methoxy-1,2,4-thiadiazol-5-yl)carbamate

HRID 1485367Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1485367
[CH3:1][O:2][C:3]1[N:7]=[C:6]([NH2:8])[S:5][N:4]=1.[C:9](Cl)(=[O:17])[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.O>ClCCl>[C:11]1([O:10][C:9](=[O:17])[NH:8][C:6]2[S:5][N:4]=[C:3]([O:2][CH3:1])[N:7]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 3141795-Amino-3-methoxy-1,2,4-thiadiazole

Produkt 1

HCID 89664142Phenyl (3-methoxy-1,2,4-thiadiazol-5-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Methoxy-1,2,4-thiadiazol-5-amine a (500 mg, 3.82 mmol) and phenyl carbonochloridate b (600 mg, 3.82 mmol) were dissolved in 20 mL of dichloromethane, followed by addition of triethylamine (0.8 mL, 5.73 mmol). After reacting for 16 hours, 30 mL of H2O were added into the reaction mixture to dilute the solution. The aqueous phase and organic phase were separated, the aqueous phase was extracted with dichloromethane (20 mL×2), and the organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography with elution system A to obtain the title product phenyl(3-methoxy-1,2,4-thiadiazol-5-yl)carbamate c (200 mg, yield 20.8%) as a white solid.

Aufarbeitung

  1. additionto dilute the solution
  2. customThe aqueous phase and organic phase were separated
  3. extractionthe aqueous phase was extracted with dichloromethane (20 mL×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography with elution system

Quellen und Nachweise

ORD-Eintrag
ord-b4051da75b034c87b5f5f3736894c63d
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422300B2

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