تفاعل #1053253

معادلة التفاعل

1,1′-carbonyldiimidazole

2-bromo-4-methylaniline

(4S,5S)-amine

(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-amine

→

title compound

المردود 20.0%

1-(2-Bromo-4-methyl-phenyl)-3-((4S,5S)-2,2-dimethyl-4-phenyl-[1,3]dioxan-5-yl)-urea

المردود 20.0%

المذيبات

N,N-dimethylformamide

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction was heated to 50° C
2. 2
   درجة الحرارةThe reaction was heated to 100° C. for 4 h
3. 3
   درجة الحرارةcooled to 25° C.
4. 4
   تركيزpartially concentrated under reduced pressure
5. 5
   غسيلwashed with water
6. 6
   تركيزThe organic layers were concentrated to a cream-colored solid
7. 7
   أخرىthat was purified by column chromatography (dichloromethane/ethyl acetate/hexane)

الإجراء التجريبي

To a stirred solution of 285 mg (1.76 mmol) of 1,1′-carbonyldiimidazole and 5 mg (0.041 mmol) of 4-(dimethylamino)pyridine in N,N-dimethylformamide (3.0 mL) was added 0.22 mL (1.76 mmol) of 2-bromo-4-methylaniline. After stirring for 15 min at 25° C., the reaction was heated to 50° C. At 50° C., a solution of 184 mg (0.88 mmol) of (4S,5S)-amine 1 in N,N-dimethylformamide (1 mL) was added dropwise. The reaction was heated to 100° C. for 4 h and then cooled to 25° C. and partially concentrated under reduced pressure. The mixture was taken up in approximately 100 mL of dichloromethane and washed with water. The organic layers were concentrated to a cream-colored solid that was purified by column chromatography (dichloromethane/ethyl acetate/hexane) to yield 73 mg (20%) of the title compound as a white foam.

المصدر