Sodium hydride → 2-[4,5-Bis-(p-methoxyphenyl)-thiazol-2-ylthio]-2-formylacetic acid ethyl ester
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[S:12][C:11](=[S:22])[N:10]=2)=[CH:5][CH:4]=1.[Na].[H-].[Na+].[CH2:26]([O:28][C:29](=[O:34])[CH2:30][C:31](Br)=[O:32])[CH3:27]>CN(C)P(=O)(N(C)C)N(C)C.C(OCC)C.CCCCCC>[CH2:26]([O:28][C:29](=[O:34])[CH:30]([S:22][C:11]1[S:12][C:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=1)[CH:31]=[O:32])[CH3:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
3.3 g of 4,5-bis-(p-methoxyphenyl)-thiazoline-2-thione are dissolved in 50 ml of hexamethylphosphoric acid triamide, the solution is cooled to 5° and converted into the sodium salt under nitrogen with sodium hydride (0.5 g of a 50% strength suspension in mineral oil, de-oiled with hexane). The product is allowed to warm to room temperature, 2.0 g of 2-bromoformylacetic acid ethyl ester are added dropwise and the mixture is stirred at 25° for 1 hour, poured into 750 ml of ice-water and taken up in diethyl ether. The ethereal phase is washed with water, dried over magnesium sulphate and concentrated to dryness by evaporation. 2-[4,5-bis-(p-methoxyphenyl)-thiazol-2-ylthio]-2-formylacetic acid ethyl ester is obtained, which can be used without further purification.
Workup
- temperaturethe solution is cooled to 5°
- washThe ethereal phase is washed with water
- dry with materialdried over magnesium sulphate
- concentrationconcentrated to dryness by evaporation
Sources & evidence
- ORD record
- ord-6b038100b6d8430d896ce0aec8fc3af8
- Source dataset
- uspto-grants-1984_05
- Patent number
- US04451471
Reaction notes
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