Phenylacetaldehyde → 5-Phenylthiazole

HRID 1649561

Reaktionsgleichung

Reaktionsgleichung von HRID 1649561
[C:1]1([C:7]2[S:11][CH:10]=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:14]=O.[C:22]1([CH2:28][CH:29]=O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.BrBr.C=S.[C:35]([NH2:38])(=[S:37])[CH3:36].[NH2:39][C:40]([NH2:42])=[S:41].[CH2:43]([NH:45][C:46](=[S:48])[O-:47])[CH3:44]>CO>[C:1]1([C:7]2[S:11][CH:10]=[N:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH3:36][C:35]1[S:37][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][N:38]=1.[NH2:42][C:40]1[S:41][C:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:29][N:39]=1.[OH:47][C:46]1[S:48][C:44]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:43][N:45]=1

Komponenten

13

Edukt 8

HCID 998PhenylacetaldehydeHCID 24408BromineHCID 79115ThioformaldehydeHCID 5952095-PhenylthiazoleHCID 2723790ThioureaHCID 2723949ThioacetamideHCID 108889012-Bromo-2-phenylacetaldehyde2×HCID 178465499HCID 178465499, Verbindung

Produkt 4

HCID 5952095-PhenylthiazoleHCID 8731195-Phenyl-thiazol-2-ylamineHCID 123675102-Methyl-5-phenyl-1,3-thiazoleHCID 178517639HCID 178517639, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In synthesis of 5-phenylthiazole derivatives, the intermediate α-bromo-α-phenylacetaldehyde is first synthesized by allowing phenylacetaldehyde to react with bromine according to the method as disclosed in Helv. Chim. Acta. Vol. 30, pp.2058 (1945). As the next step, according to the method disclosed in J. Amer. Chem. Soc. Vol. 71, pp.4007 (1949), α-bromo-α-phenylacetaldehyde is allowed to react respectively with thioformaldehyde, thioacetamide, thiourea and ethylthiocarbamate at room temperature in methanol as a reaction solvent to obtain 5-phenylthiazole (m.p. 45°-46° C.), 2-methyl-5-phenylthiazole (m.p. 74°-76° C.), 2-amino-5-phenylthiazole (m.p. 206°-208° C.) and 2-hydroxy-5-phenylthiazole (m.p. 202°-204° C.). On the other hand, according to the method as described in U.S. Pat. No. 2,603,646 (1952), phenylacetaldehyde is allowed to react with thiocyanogen to obtain α-phenyl-α-thiocyanoacetaldehyde, which is then allowed to react with ammonium dithiocarbamate in the presence of an acid catalyst such as dilute sulfuric acid to obtain 2-mercapto-5-phenylthiazole (m.p. 207°-209° C.).

Quellen und Nachweise

ORD-Eintrag
ord-5e34c6bcd2774192bdbdede10a6416a1
Quelldatensatz
uspto-grants-1983_11
Patentnummer
US04418070

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