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COOH
O
H
O
COCl 2
O
O
N
N
Cl
H 2 N
N
NH
S
N
H
S
H
O
O
O
O
O
153
154
155
COOH
O
O
N
H
N
O
N
N
S
N
H
H
O
O
O
156
Mezlocillin
O
O
H
N
O
HN
Cl
H 2 N
O
N
O
O
O
O
159
COCl 2
N
N
H
N
H
157
158
160
Na
D
OH
Cl
N
N
N
Cl
N
NH
N
N
N
162
N
N
Cl
O
O
O
O
1. NaOH
2. HCl
161
163
Nefazodone hydrochloride
Triazolone 167, a useful building block for APIs such as Nefazodone or Eto-
peridone [52942-31-1] 168, an antidepressant, can be obtained from 5-ethyl-1,3,4-
oxadiazolinone 165, which, in turn, is prepared by phosgenation of propionyl
hydrazide 164 without the need for the highly toxic ethyl isocyanate [127].
Nilutamide [63612-50-0], non-steroidal antiandrogen ( for treatment of prostatic carci-
noma), 173.
3-Fluoromethyl-4-nitrophenyl
isocyanate 170 is synthesized with
phosgene [128-130].
 
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