Acetic Acid → 2-[4,5-Bis-(p-methoxyphenyl)-thiazol-2-ylthio]-acetaldehyde
Reaction equation
C[O:2][CH:3](OC)[CH2:4][S:5][C:6]1[S:7][C:8]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:10]=1.C(O)(=O)C.S(=O)(=O)(O)O.O>C(OCC)(=O)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:10]=[C:6]([S:5][CH2:4][CH:3]=[O:2])[S:7][C:8]=2[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:12][CH:13]=1Participants
6
Procedure
7.0 g of 2-[4,5-bis-(p-methoxyphenyl)-thiazol-2-ylthio]-acetaldehyde-dimethylacetal are mixed with 50 ml of acetic acid, 25 ml of sulphuric acid and 25 ml of water, stirred vigorously for 30 minutes, and then stirred into 1000 ml of ice-water. The oil which separates is taken up in 200 ml of ethyl acetate. Shaking is carried out with a further 200 ml of ethyl acetate and the combined organic phases are washed with water and then twice with cold sodium bicarbonate solution, dried over magnesium sulphate and concentrated to dryness by evaporation. The crude product is crystallised with diethyl ether. 2-[4,5-bis-(p-methoxyphenyl)-thiazol-2-ylthio]-acetaldehyde having a melting point of 75°-76° is obtained.
Workup
- stirringShaking
- washthe combined organic phases are washed with water
- dry with materialtwice with cold sodium bicarbonate solution, dried over magnesium sulphate
- concentrationconcentrated to dryness by evaporation
- customThe crude product is crystallised with diethyl ether
Sources & evidence
- ORD record
- ord-dd213e223f904ea895d9f60ffebc329f
- Source dataset
- uspto-grants-1984_05
- Patent number
- US04451471
Reaction notes
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