تفاعل #343795

معادلة التفاعل

[[5-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]-1,3,4-thiadiazol-2-yl]thio]acetic acid

dicyclohexylcarbodiimide

1-hydroxybenzotriazole

N-methylhydroxylamine.hydrochloride

→

2-[[5-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]-1,3,4-thiadiazol-2-yl]thio]-N-hydroxy-N-methylacetamide

المردود 36.8%

المذيبات

ethyl acetate

tetrahydrofuran

ethyl acetate

N,N-dimethylformamide

triethylamine

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   ترشيحThen, insoluble matters were filtered off
3. 3
   أخرىthe filtrate thus formed
4. 4
   تركيزwas concentrated under reduced pressure
5. 5
   أخرىTo the residue thus formed
6. 6
   غسيلthe mixture was washed with water
7. 7
   غسيلwashed with a diluted aqueous solution of sodium hydrogencarbonate, and water
8. 8
   تجفيفdried over anhydrous magnesium sulfate
9. 9
   تركيزconcentrated under reduced pressure
10. 10
    أخرىTo the residue thus obtained
11. 11
    ترشيحinsoluble materials were filtered off
12. 12
    أخرىthe filtrate formed
13. 13
    تركيزwas concentrated
14. 14
    أخرىThe residue thus obtained
15. 15
    أخرىwas recrystallized from a mixture of toluene and n-hexane

الإجراء التجريبي

To a mixture of 0.5 g of [[5-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]-1,3,4-thiadiazol-2-yl]thio]acetic acid obtained in example 22, 0.23 g of dicyclohexylcarbodiimide, 0.14 g of 1-hydroxybenzotriazole, and 50 ml of tetrahydrofuran was added a mixture of 0.27 g of N-methylhydroxylamine.hydrochloride, 0.3 g of triethylamine, and 5 ml of N,N-dimethylformamide and the resultant mixture was stirred overnight at room temperature. Then, insoluble matters were filtered off and the filtrate thus formed was concentrated under reduced pressure. To the residue thus formed was added 100 ml of ethyl acetate and the mixture was washed with water, washed with a diluted aqueous solution of sodium hydrogencarbonate, and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue thus obtained was added ethyl acetate, then insoluble materials were filtered off and the filtrate formed was concentrated. The residue thus obtained was recrystallized from a mixture of toluene and n-hexane to provide 0.18 g of 2-[[5-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]-1,3,4-thiadiazol-2-yl]thio]-N-hydroxy-N-methylacetamide.

المصدر