Ethyl isothiocyanate → Methyl 5-(ethylamino)-2-(methylthio)-4-thiazolecarboxylate
Reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][N:5]=[C:6]([S:9][CH3:10])[S:7][CH3:8].CC([O-])(C)C.[K+].[CH2:18]([N:20]=C=S)[CH3:19]>C1COCC1>[CH3:10][S:9][C:6]1[S:7][C:8]([NH:20][CH2:18][CH3:19])=[C:4]([C:3]([O:2][CH3:1])=[O:11])[N:5]=1Participants
Procedure
A solution of N-[Bis(methylthio)methylene]glycine methyl ester (1 mmole) in anhydrous THF (2 mL) was added to a solution of t-BuOK (1.4 mmole) in anhydrous THF (10 mL) at −78° C. and the mixture was stirred for 30 min. Then a solution of ethyl isothiocyanate (1 mmole) in anhydrous THF (2 mL) was added and the reaction was stirred at −78° C. for 30 min and at room temperature for 2 h. The reaction was quenched with water. Extraction and chromatography gave 2-methylthio-5-(N-ethylamino)-4-methoxycarbonylthiazole as a yellow solid, which was subjected to Step B and C of Example 18 followed by Step C of Example 3 to give 2-methylthio-5-(N-ethylamino)-4-phosphonomethoxycarbonylthiazole (18.4) as a solid. Mp>200° C. (decomp). Anal. Calcd. for C8H13N2O5PS2+0.1 HBr: C: 29.99; H: 4.12; N: 8.74. Found: C: 29.71; H: 4.10; N: 8.60.
Workup
- stirringthe reaction was stirred at −78° C. for 30 min and at room temperature for 2 h
- customThe reaction was quenched with water
- extractionExtraction and chromatography
Sources & evidence
- ORD record
- ord-bb353c4d4ccf495987f63bd4e593a500
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06756360B1
Reaction notes
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