Ethyl bromoacetate → [[5-[4-(1,1-Dimethylethyl)phenyl]-1,2,3-thiadiazol-4-yl]thio]acetic acid ethyl ester

HRID 1381714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1381714
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][N:14]=[N:13][C:12]=2[SH:16])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[K].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][S:16][C:12]1[N:13]=[N:14][S:15][C:11]=1[C:8]1[CH:7]=[CH:6][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[CH:10][CH:9]=1)[CH3:24]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 5462222PotassiumHCID 14294241HCID 14294241, Verbindung

Produkt 1

HCID 14294226[[5-[4-(1,1-Dimethylethyl)phenyl]-1,2,3-thiadiazol-4-yl]thio]acetic acid ethyl esterAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2.9 g of 5-[4-(1,1-dimethylethyl)phenyl]-1,2,3-thiadiazole-4-thiol, potassium salt in 50 ml of ethanol was stirred overnight with 1.67 g of ethyl bromoacetate, then concentrated in vacuo. The residue was taken up in ether, filtered and evaporated in vacuo. The oily residue was dissolved in dichloromethane and purified as described in Example 50, giving an oil which was crystallized from methylcyclohexane, giving 2.8 g of the desired compound as white needles, mp 62.5°-63.5° C. Proton nuclear magnetic resonance (δ[ppm], CDCl3) 90 MHz: 1.21 (t, 3H, J=7.0 Hz, CH3); 1.37 (s, 9H, t-butyl); 4.11 (s, 2H, SCH2); 4.15 (q, 2H, CH2O); 7.55 (s, 4H, C6H4). Infrared absorption spectrum (KBr pellet): 1739(s); 1606(w); 1520(w); 1480(w); 1445(w); 1385(w); 1365(w); 1305(s); 1175(s); 1040(w); 935(s); 840(s).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. dissolutionThe oily residue was dissolved in dichloromethane
  5. custompurified
  6. customgiving an oil which
  7. customwas crystallized from methylcyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-e23cda9cbd564287a057d2ad2b668662
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04803280

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