DAI Liyan, HU Weiya, WANG Xiaozhong, et al. Novel synthesis process of 5H-dibenz[b,f]azepine and removal of chloroformyl protection group[J]. CIESC Journal, 2008, (9): 2419-2423.
DAI Liyan, HU Weiya, WANG Xiaozhong, et al. Novel synthesis process of 5H-dibenz[b,f]azepine and removal of chloroformyl protection group[J]. CIESC Journal, 2008, (9): 2419-2423.DOI:
f]azepine was studied.It is an important intermediate of 5H-dibenz[b
f]azepine-5-carboxamide
used in genetic engineering
materials science and so on.With 10
11-dihydro-5H-dibenz[b
f]azepine as raw material
5-chloroformyl-5H-dibenz[b
f]azepine was prepared by reflux with triphosgene in toluene
brominated with bromine in chlorobenzene
and dehydrobrominated at 130℃
finally
the title compound was obtained by removing chloroformyl group with NaOH in isopropanol with 80.4% overall yield.The optimal reaction conditions and yields (temperature
time
molar yield) were as follows: acyl chlorination
110℃
10 h
93.0%;bromination
dehydrobromination
100℃
2 h
130℃
5 h
88.0%;removal of chloroformyl group
40℃
3 h
98.2%. The melting point of the title compound was the same as literature reported
and its structure was confirmed by 1H NMR.The optimal technology condition to remove chloroformyl group as protection group and its application of protection for some amine compounds were also studied.