Toluene → HCID 10847849, compound
Reaction equation
[CH2:1]([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[N:10]=[C:9]1O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.P(Cl)(Cl)([Cl:27])=O>>[CH2:1]([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[N:10]=[C:9]1[Cl:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
Grams 21 3-benzyl-2-hydroxy-3H-imidazo[4,5-b]pyridine in 330 ml phosphoryl chloride are refluxed until complete dissolution then gaseous hydrogen chloride is bubbled therein for 3 and a half hours. It is then cooled to room temperature and the undissolved product filtered and washed with toluene; the solution is evaporated in vacuo to a small volume and cautiously poured into ice. The solution is then filtered on charcoal and the filtrate adjusted to pH 7.5 by adding 30% ammonium hydroxyde. The undissolved product is separated by filtration, washed with water ed evaporated in vacuo to dryness, the product thus obtained suspended in 150 ml boiling toluene and the undissolved product filtered off. From the toluene solution are obtained by crystallization 5 g 3-benzyl-2-chloro-3H-imidazo[4,5-b]pyridine melting at 74°-76° C.
Workup
- customgaseous hydrogen chloride is bubbled
- customfor 3 and a half hours
- filtrationthe undissolved product filtered
- washwashed with toluene
- customthe solution is evaporated in vacuo to a small volume
- additioncautiously poured into ice
- filtrationThe solution is then filtered on charcoal
- additionby adding 30% ammonium hydroxyde
- customThe undissolved product is separated by filtration
- washwashed with water
- customed evaporated in vacuo to dryness
- customthe product thus obtained
- filtrationthe undissolved product filtered off
Sources & evidence
- ORD record
- ord-c07ba730bf1142289269320b970e7677
- Source dataset
- uspto-grants-1991_06
- Patent number
- US05023256
Reaction notes
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