2-Amino-5-chloropyridine → HCID 23345083, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Cl:9][C:10]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:11]=1[C:12]([N:14]=[C:15]=[O:16])=[O:13]>ClCCCl>[Cl:9][C:10]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:11]=1[C:12]([NH:14][C:15]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1)=[O:16])=[O:13]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
5-Chloro-2-aminopyridine (450 grams; 3.5 moles) and 5000 ml. of 1,2-dichloroethane were slurried together. The flask was then purged with nitrogen and a cold water bath applied, resulting in a lowering of the temperature to 20° C. 2,6-Dichlorobenzoyl isocyanate (912 grams; 4.2 moles) was added dropwise over one hour, holding the temperature at <30° C. The reaction mixture was stirred for 10 minutes, the cold water bath was removed, and a hot tap water bath (about 55° C.) was applied. The flask temperature rose to 42° C. and was held at 40° C. for 30 minutes. TLC showed that all starting material had been reacted. Solvent was removed on a rotary evaporator, and the solid residue was slurried with 1 liter of methanol, chilled and filtered. Yield was 1177 grams. m.p. 219°-222° C. Identity of the product was confirmed by NMR and IR.
Workup
- customThe flask was then purged with nitrogen and a cold water bath
- customresulting in
- customa lowering of the temperature to 20° C
- customat <30° C
- customthe cold water bath was removed
- customa hot tap water bath (about 55° C.) was applied
- customrose to 42° C.
- waitwas held at 40° C. for 30 minutes
- customhad been reacted
- customSolvent was removed on a rotary evaporator
- temperaturechilled
- filtrationfiltered
Sources & evidence
- ORD record
- ord-c5c5b739e52340cf8e020a0be6819081
- Source dataset
- uspto-grants-1980_08
- Patent number
- US04219557
Reaction notes
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