Water → Phenyl(6-thiocyanato-1,3-benzothiazol-2-yl)carbamate

HRID 517799

Reaktionsgleichung

Reaktionsgleichung von HRID 517799
[C:1](Cl)(=[O:9])[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+].O.[NH2:17][C:18]1[S:19][C:20]2[CH:26]=[C:25]([S:27][C:28]#[N:29])[CH:24]=[CH:23][C:21]=2[N:22]=1>O1CCCC1>[S:27]([C:25]1[CH:24]=[CH:23][C:21]2[N:22]=[C:18]([NH:17][C:1](=[O:9])[O:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[S:19][C:20]=2[CH:26]=1)[C:28]#[N:29]

Komponenten

6

Edukt 4

HCID 962WaterHCID 15891Phenyl chloroformateHCID 816002-Amino-6-thiocyanato-1,3-benzothiazoleHCID 516892Sodium Bicarbonate

Produkt 1

HCID 53472570Phenyl(6-thiocyanato-1,3-benzothiazol-2-yl)carbamateAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

7.5 g of phenyl chlorocarbonate and then 4.05 g of sodium hydrogen carbonate and 9.4 cm3 of water are added, at 20° C., to a solution of 2.5 g of commercial 2-amino-1,3-benzothiazol-6-yl thiocyanate in 94 cm3 of tetrahydrofuran. The resulting mixture is subsequently stirred at 20° C. for 20 h and then extracted with 2×150 cm3 of ethyl acetate. The organic phases are combined and then washed with 3×50 cm3 of a saturated aqueous solution of sodium hydrogen carbonate. The organic phase obtained is dried over magnesium sulphate and then concentrated to dryness under reduced pressure. The residue is taken up in 50 cm3 of water and the product is spin-filter-dried and dried under vacuum at 20° C. 3.45 g of phenyl (6-thiocyanato-1,3-benzothiazol-2-yl)carbamate are thus obtained in the form of a pale yellow solid, the characteristics of which are as follows:

Aufarbeitung

  1. extractionextracted with 2×150 cm3 of ethyl acetate
  2. washwashed with 3×50 cm3 of a saturated aqueous solution of sodium hydrogen carbonate
  3. customThe organic phase obtained
  4. dry with materialis dried over magnesium sulphate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customthe product is spin-filter-dried
  7. customdried under vacuum at 20° C

Quellen und Nachweise

ORD-Eintrag
ord-789fd4d4ec1a4d488f529b42e8d9665e
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115134B2

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