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Dimethoxanate [477-93-0], antitussive, 80. The synthesis includes as a key step the
phosgenation of phenothiazine 77 to form the corresponding carbamoyl chloride
78 [55].
O
l
H
N
N
COCl 2
pyridine
S
S
77
78
O
N
O
HO
N
O
O
N
79
S
80
Dimethoxanate
Distigmine bromide [15876-67-2], parasympathomimetic, 85. N,N,N 0 ,N 0 -Tetrame-
thylhexamethylenediamine 81 is demethylated and chlorocarbonylated with phos-
gene to form the corresponding bis(carbamoyl chloride) 82, the key intermediate in
the synthesis of Distigmine bromide 85 [54].
O
l
COCl 2
N
N
N
N
81
O
l
82
HO
N
83
N
N
Br
O
O
O
O
CH 3 Br
N
N
N
N
O
O
O
O
84
N
85
N
Distigmine bromide
Br
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