Ethyl chloroformate → Ethyl N-(5,5,7,7-Tetramethyl-4,5,6,7-tetrahydrobenzothiazol-2-yl)carbamate

HRID 2058851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2058851
[NH2:1][C:2]1[S:3][C:4]2[C:10]([CH3:12])([CH3:11])[CH2:9][C:8]([CH3:14])([CH3:13])[CH2:7][C:5]=2[N:6]=1.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17]>N1C=CC=CC=1>[CH3:13][C:8]1([CH3:14])[CH2:7][C:5]2[N:6]=[C:2]([NH:1][C:16](=[O:17])[O:18][CH2:19][CH3:20])[S:3][C:4]=2[C:10]([CH3:12])([CH3:11])[CH2:9]1

Komponenten

4

Edukt 2

HCID 10928Ethyl chloroformateHCID 127833484,5,6,7-tetrahydro-5,5,7,7-tetramethyl-2-Benzothiazolamine

Produkt 1

HCID 20548456Ethyl N-(5,5,7,7-Tetramethyl-4,5,6,7-tetrahydrobenzothiazol-2-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

2-Amino-5,5,7,7-tetramethyl-4,5,6,7-tetrahydrobenzothiazole (16 grams; 0.075 mol) dissolved in pyridine (100 ml) was charged into a glass reaction vessel equipped with a mechanical stirrer and addition funnel. Ethyl chloroformate (11 grams; 0.1 mol) was then added dropwise with stirring and cooling of the reaction mixture. After the addition was completed the reaction mixture was allowed to warm to room temperature and stirring was continued for a period of about 1 hour. After this time the reaction mixture was poured into ice water resulting in a white precipitate. The precipitate was recovered by filtration, was dried and recrystallized from methanol to yield the desired product ethyl N-(5,5,7,7-tetramethyl-4,5,6,7-tetrahydrobenzothiazol-2-yl) carbamate having a melt point of 124° to 125° C.

Aufarbeitung

  1. additionwas charged into a glass reaction vessel
  2. customequipped with a mechanical stirrer and addition funnel
  3. temperaturecooling of the reaction mixture
  4. additionAfter the addition
  5. stirringstirring
  6. filtrationThe precipitate was recovered by filtration
  7. customwas dried
  8. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-84f411cbf742456bba4adb9342980d89
Quelldatensatz
uspto-grants-1982_03
Patentnummer
US04319914

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