反应 #302894

反应方程式

((2,3-dimethylphenyl)methyl)-1,3-thiazolin-2-ylamine

methyl chloroformate

sodium hydride

→

N-((2,3-dimethylphenyl)methyl)methoxy-N-(1,3-thiazolin-2-yl)carboxamide

收率 45.7%

溶剂

brine

THF

THF

反应条件

后处理

1. 1
   workup.ADDITIONwas added slowly
2. 2
   温度The reaction mixture was heated to 60° C. where it
3. 3
   workup.STIRRINGstirred for one hour
4. 4
   萃取extracted with two 25 mL portions of ethyl acetate
5. 5
   洗涤washed with 25 mL of water
6. 6
   干燥dried with sodium sulfate
7. 7
   过滤filtered
8. 8
   浓缩The filtrate was concentrated under reduced pressure
9. 9
   其他to leave a solid residue
10. 10
    其他The residue was purified by column chromatography on silica gel
11. 11
    洗涤eluting with hexanes:methylene chloride (1:1)
12. 12
    浓缩concentrated under reduced pressure

实验过程

Under a dry nitrogen atmosphere, a solution of 0.25 gram (0.0011 mole) of ((2,3-dimethylphenyl)methyl)-1,3-thiazolin-2-ylamine dissolved in 10 mL of THF was added to a stirred suspension of 0.08 gram (0.0012 mole) of sodium hydride (60% suspension in oil). The mixture was stirred for 30 minutes, at which time a solution of 0.11 mL (0.0014 mole) of methyl chloroformate in 5 mL of THF was added slowly. The reaction mixture stirred at ambient temperature for about 18 hours. The reaction mixture was heated to 60° C. where it stirred for one hour. The reaction mixture was diluted with 25 mL of brine, then extracted with two 25 mL portions of ethyl acetate. The extracts were combined, washed with 25 mL of water, dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to leave a solid residue. Analysis of the residue by TLC indicated that two compounds were present. The residue was purified by column chromatography on silica gel, eluting with hexanes:methylene chloride (1:1). The appropriate fractions were combined and concentrated under reduced pressure to yield 0.05 gram of methyl 2-(1-aza-2-(2,3-dimethylphenyl)ethylidene)-1,3-thiazolidine-3-carboxylate (Compound C53) and 0.14 gram of N-((2,3-dimethylphenyl)methyl)methoxy-N-(1,3-thiazolin-2-yl)carboxamide (Compound D5). The NMR spectra were consistent with the proposed structures.

来源