Ethyl thiocyanate → (2-Amino-benzothiazol-6-yl)-acetic acid ethyl ester

HRID 1790387

Reaktionsgleichung

Reaktionsgleichung von HRID 1790387
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.C([S:16][C:17]#[N:18])C.BrBr.[OH-].[Na+]>C(O)(=O)C>[NH2:18][C:17]1[S:16][C:7]2[CH:6]=[C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]=[CH:3][C:2]=2[N:1]=1

Komponenten

6

Edukt 4

HCID 10968Ethyl thiocyanateHCID 14798Sodium HydroxideHCID 24408BromineHCID 225219p-Aminophenylacetic acid ethyl ester

Produkt 1

HCID 821202(2-Amino-benzothiazol-6-yl)-acetic acid ethyl esterAusbeute 93,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

Ethyl 4-aminophenylacetate (18 g) was dissolved in acetic acid (120 ml) and ethyl thiocyanate (29.3 g) was added thereto. Under ice cooling, bromine (6.2 ml) was added dropwise thereinto over 45 minutes while maintaining the reaction temperature at about 10° C. After the completion of the addition, the resultant mixture was stirred at room temperature for 1.5 hr and then at 80° C. for about 2 hr until the reaction was completed. Then the reaction solution was poured into ice water, basified with an 8 N aqueous solution of sodium hydroxide, extracted with chloroform, washed with water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give the title compound (22.23 g) as orange crystals (yield: 93.66%).

Aufarbeitung

  1. additionAfter the completion of the addition
  2. extractionextracted with chloroform
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-95b25d98d1334363b00baa78d11a4e52
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071201B2

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