반응 #1269841

반응 방정식

Ethyl formate

sarcosin methyl ester hydrochloride

NaH

HCl

HCl

K2CO3

ethanol

H2NCN

sodium acetate

→

1-N-methyl-2-amino imidazole-5-carboxylic acid ethyl ester

용매

HOAc

반응 조건

후처리

1. 1
   기타to reaction)
2. 2
   기타contained in a 1-L round-bottomed flask
3. 3
   온도The reaction mixture was cooled in an ice-water bath
4. 4
   workup.ADDITIONadded slowly during a period of 2 h
5. 5
   workup.STIRRINGstirred at rt for about 14 h
6. 6
   기타Volatiles were removed
7. 7
   기타a rotary evaporator
8. 8
   기타to yield a residue which
9. 9
   기타was triturated twice with hexane (500 mL)
10. 10
    기타to yield a sticky light brown paste which
11. 11
    온도After the reaction mixture cooled
12. 12
    여과the white precipitate was filtered off
13. 13
    세척the residue washed with 2×25 mL of ethanol
14. 14
    기타The filtrate was evaporated
15. 15
    기타to yield a thick brown oil to which
16. 16
    workup.STIRRINGThe reaction mixture was stirred at 90-100° C. for 1.5 h
17. 17
    기타to yield a clear solution which
18. 18
    온도was cooled
19. 19
    농축the resulting solution concentrated
20. 20
    기타a rotary evaporator at a temperature not more than 45° C
21. 21
    기타The concentrated reaction mixture
22. 22
    추출extracted with EA (5×200 mL followed by 3×50 mL)
23. 23
    건조The combined ethyl acetate layers were dried over MgSO4
24. 24
    여과filtered
25. 25
    기타volatiles removed

실험 절차

Ethyl formate (500 mL) was added to sarcosin methyl ester hydrochloride (82 g, 585.7 mmol, grounded into powder prior to reaction) contained in a 1-L round-bottomed flask. The reaction mixture was cooled in an ice-water bath, stirred, a gas outlet connected with the flask, NaH (60% oil suspension, 54 g, 1.35 mol) added slowly during a period of 2 h, and stirred at rt for about 14 h. Volatiles were removed using a rotary evaporator to yield a residue which was triturated twice with hexane (500 mL) to yield a sticky light brown paste which was dissolved in ethanol (400 mL) and conc. HCl (50 mL) and stirred at 110° C. for 1.5 h. After the reaction mixture cooled, the white precipitate was filtered off and the residue washed with 2×25 mL of ethanol. The filtrate was evaporated to yield a thick brown oil to which was added 10% aqueous HOAc, H2NCN (45 g, 1.07 mol), and sodium acetate (88 g, 1.07 mol). The reaction mixture was stirred at 90-100° C. for 1.5 h to yield a clear solution which was cooled, its pH adjusted to 1 using concentrated HCl and the resulting solution concentrated to ⅕ its original volume using a rotary evaporator at a temperature not more than 45° C. The concentrated reaction mixture was carefully neutralized by addition of K2CO3 to a pH of 8-9 and extracted with EA (5×200 mL followed by 3×50 mL). The combined ethyl acetate layers were dried over MgSO4, filtered, and volatiles removed to yield 48 g of 1-N-methyl-2-amino imidazole-5-carboxylic acid ethyl ester.

출처