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New and convergent synthesis of saflufenacil
Author(s) -
Wang Bin,
Mao Yongjun,
Liu Xiangyu,
Zhao Zhiwei,
Bu Lehao,
Wang Han
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3757
Subject(s) - chemistry , isopropylamine , yield (engineering) , isocyanate , sulfamide , isopropyl , hydroxylamine , organic chemistry , materials science , metallurgy , polyurethane
A new, practical, and hundred‐gram scale synthesis of saflufenacil, a protoporphyrinogen oxidase (PPO) inhibitor herbicide, is described. The key intermediate N ‐methyl‐ N ‐isopropyl sulfamide ( 12 ) is obtained from sulfuryl chloride isocyanate, t ‐butanol, and N ‐methyl‐ N ‐isopropylamine in 74.8% yield over 3 steps. Saflufenacil is prepared in 48.6% yield over 8 steps and 98.7% purity (HPLC).
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