2-Amino-4-(p-nitrophenyl)thiazole → 2,2,2-trichloroethyl N-(4-p-nitrophenyl-2-thiazolyl)carbamate
Reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)[N:6]=1.C(=O)([O-])O.[Na+].Cl[C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23]>CC(C)=O.C(OCC)C>[N+:13]([C:10]1[CH:9]=[CH:8][C:7]([C:5]2[N:6]=[C:2]([NH:1][C:22](=[O:23])[O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])[S:3][CH:4]=2)=[CH:12][CH:11]=1)([O-:15])=[O:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Into 300 ml of acetone, were added 2.2 g of 2-amino-4-p-nitrophenylthiazole and 3.0 g of sodium hydrogen carbonate. To the resulting mixture, 6.3 g of 2,2,2-trichloroethyl chloroformate in 20 ml of acetone was added dropwise, followed by a stirring for 10 hours at the reflux temperature. Inorganic substances were filtered off and the filtrate was concentrated. Any substances, which were insoluble in diethyl ether, were removed from the concentrate. A crude reaction product resulting from the remaining portion, which was soluble in diethyl ether, was subjected to silica gel column chromatography. It was then eluted with a mixed solvent of chloroform-acetone (10:1) and thereafter recrystallized from chloroform to obtain 2.7 g of 2,2,2-trichloroethyl N-(4-p-nitrophenyl-2-thiazolyl)carbamate.
Workup
- customstirring for 10 hours
- filtrationInorganic substances were filtered off
- concentrationthe filtrate was concentrated
- customwere removed from the concentrate
- customA crude reaction product
- customresulting from the remaining portion, which
- washIt was then eluted with a mixed solvent of chloroform-acetone (10:1)
- customrecrystallized from chloroform
Sources & evidence
- ORD record
- ord-152a42a338c14cfe9fec224e95c50be4
- Source dataset
- uspto-grants-1985_04
- Patent number
- US04511574
Reaction notes
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