Diethyl Ether → HCID 178512478, compound
Reaction equation
O[C:2]1[C:7]([CH2:8][C:9]2[N:10]=[CH:11][NH:12][CH:13]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[C:14](=[NH:17])OC.[OH2:18].[NH2:19][NH2:20].C(OCC)C>CO>[OH:18][C:2]1[C:7]([CH2:8][C:9]2[N:10]=[CH:11][NH:12][CH:13]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[C:14]([NH:19][NH2:20])=[NH:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2 g (0.0066 mole) of methyl 2-hydroxy-3-(1H-imidazol-4-ylmethyl)-benzenecarboximidate prepared in 6.a) above in 20 ml of methanol is added in one go to a solution of 1.52 ml (0.0033 mole) of hydrazine hydrate in 20 ml of methanol. The reaction is allowed to proceed for 15 minutes, then 40 ml of diethyl ether are added. The precipitate which has formed is filtered off and the filtrate is concentrated under reduced pressure. The evaporation residue is purified by preparative liquid chromatography (silica: 400 g; eluent: 89:10:1 (v/v/v) mixture of dichloromethane-methanol-ammonia). The pale yellow solid product obtained after evaporation of the solvents is recrystallized from methanol. 1.2 g of 2-hydroxy-3-(1H-imidazol-4-ylmethyl)-benzenecarboximidic acid hydrazide are obtained. Yield: 80%.
Workup
- customThe precipitate which has formed
- filtrationis filtered off
- concentrationthe filtrate is concentrated under reduced pressure
- customThe evaporation residue is purified by preparative liquid chromatography (silica: 400 g; eluent: 89:10:1 (v/v/v) mixture of dichloromethane-methanol-ammonia)
- customThe pale yellow solid product obtained
- customafter evaporation of the solvents
- customis recrystallized from methanol
Sources & evidence
- ORD record
- ord-79df7f302efd43168a8a02f34d25248d
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05385927
Reaction notes
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