Chemistry Reference
In-Depth Information
Ethinamate [126-52-3], hypnotic, sedative, 101.
The target molecule, 1-ethynylcyclo-
hexanol carbamate 101, is prepared by phosgenation of the corresponding cyclo-
hexanol 100 followed by treatment with ammonia [80, 81].
CH
CH
HO
H
2
N
O
1.
COCl
2
2. NH
3
O
100
101
Ethinamate
Febarbamate [13246-02-1], tranquilizer, 105.
Phosgenation of n-butylglycidyl ether
102 in toluene in the presence of 0.5 mol% hexabutylguanidinium chloride
(HBGCl) at 30
C for 2 h gave the corresponding 1-chloromethyl-2-n-butoxyethyl
chloroformate 103 in 96% yield [82].
O
NH
3
/H
2
O
COCl
2
O
Cl
CONH
2
Bu
n
O
Cl
COCl
O
OBu
n
OBu
n
102
103
104
OCONH
2
OBu
t
O
N
O
Et
NH
O
105
Febarbamate
Felbamate [25451-15-4], anticonvulsant, 109.
2-Phenyl-1,3-propanediol dicarbamate
109 (Felbamate) is prepared from 2-phenyl-1,3-propanediol 106 with phosgene
[83], ethyl carbamate 107 [84, 85], or chlorosulfonyl isocyanate 108 [84, 85].
1.
COCl
2
2. NH
3
O
O
O
HO
OH
H
3
CONH
2
H
2
N
O
O
NH
2
Felbamate
107
109
ClSO
2
NCO
106
108
