Trityl chloride → 4-Chloromethyl-2-tritylaminothiazole

HRID 434646

Reaktionsgleichung

Reaktionsgleichung von HRID 434646
Cl.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8][Cl:9])[N:7]=1.[C:10](Cl)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl.C(OCC)(=O)C.CN(C1C=CC=CN=1)C>[Cl:9][CH2:8][C:6]1[N:7]=[C:3]([NH:2][C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[S:4][CH:5]=1

Komponenten

7

Edukt 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)

Produkt 1

HCID 137451724-Chloromethyl-2-tritylaminothiazoleAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 218852-DimethylaminopyridineKatalysatorHCID 6212ChloroformLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-amino-4-chloromethylthiazole hydrochloride (3.701 g), trityl chloride (11.15 g), triethylamine (10.5 ml) and dimethylaminopyridine (10 mg) in chloroform (150 ml) was stirred at room temperature. After 23 h the reaction mixture was diluted with chloroform (150 ml) and then washed with 5% aqueous sodium hydrogen carbonate solution (2×50 ml) and brine (50 ml), dried (MgSO4) and evaporated to an orange gum. The gum was triturated with diethyl ether to give a pale brown solid. The liquors from the trituration were diluted with ethyl acetate (250 ml) and washed with M-hydrochloric acid (3×60 ml), water (60 ml), and brine (30 ml) dried (MgSO4) and evaporated to a pale brown foam. The triturated solid was treated in the same manner as the liquors to give a pale brown foam. The two foams were combined and subjected to column chromatography on silica developing and eluting with ethyl acetate-petrol, 1:9 and gave an off white solid (3.241 g). A portion (240 mg) of the solid was crystallised twice from ethyl acetate-petrol to give off white crystals of the title thiazole (206 mg), m.p. 139°-140° C., λmax (EtOH) 267.5 nm (ε 8,050).

Aufarbeitung

  1. washwashed with 5% aqueous sodium hydrogen carbonate solution (2×50 ml) and brine (50 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated to an orange gum
  4. customThe gum was triturated with diethyl ether
  5. customto give a pale brown solid
  6. washwashed with M-hydrochloric acid (3×60 ml), water (60 ml), and brine (30 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated to a pale brown foam
  9. additionThe triturated solid was treated in the same manner as the liquors
  10. customto give a pale brown foam
  11. washeluting with ethyl acetate-petrol, 1:9

Quellen und Nachweise

ORD-Eintrag
ord-3951e12837cd4b809a7e072f3e369a51
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04399140

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