반응 #73095

반응 방정식

thiazole-2-carbonitrile

nBuLi

2,2-dimethoxyethanamine

Ammonia

→

2-(1H-imidazol-2-yl)thiazole

용매

hexane

THF

반응 조건

후처리

1. 1
   workup.STIRRINGthe resulting solution was stirred at 0° C. for 2 h
2. 2
   기타quenched with 20 mL of 5% MeOH in water
3. 3
   기타The volatiles were removed
4. 4
   workup.ADDITION6N HCl was added
5. 5
   온도The acidic solution was refluxed overnight
6. 6
   workup.ADDITIONthen poured into a mixture of ice and aqueous Na2CO3
7. 7
   추출This was extracted with EtOAc
8. 8
   농축the organic layer was concentrated
9. 9
   기타to give Imadazole 2

실험 절차

A 2.5 M solution of nBuLi (2.0 eq) in hexane was added under argon to a solution of 2,2-dimethoxyethanamine (2.0 eq) in THF at −78° C. After stirring for 30 min, thiazole-2-carbonitrile (2-Im-2, 3.0 g, 1.0 eq) was added and the resulting solution was stirred at 0° C. for 2 h, then quenched with 20 mL of 5% MeOH in water. The volatiles were removed and 6N HCl was added to adjust to pH=1. The acidic solution was refluxed overnight, cooled to rt then poured into a mixture of ice and aqueous Na2CO3. This was extracted with EtOAc and the organic layer was concentrated to give Imadazole 2. LCMS (0.01% Ammonia): 152.1 m/z (M+H)+; 1H-NMR (DMSO-d6, 500 MHz): δ: 13.19 (bs, 1H), 7.98 (d, 1H, J=3.0 Hz), 7.82 (d, 1H, J=3.0 Hz), 7.36 (s, 1H), 7.14 (s, 1H).

출처