Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | HCID 178485324 | HCID 178485324 | — |
| Reactant | HCID 178497710 | HCID 178497710 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 178485323 | HCID 178485323 | 71% |
Reaction Steps
2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-N-methylbenzamide hydrochloride. 6.96 g (30 mmoles) of methyl 2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-benzoate (prepared in Example 1.B.2.) and 60 ml of methylamine dissolved in 350 ml of ethanol, are heated in an autoclave at 75° C. for 3 hours. The mixture is evaporated under reduced pressure. The residue is taken up in water and extracted three times with ethyl acetate. The organic phase is dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue is purified by chromatography on silica gel (eluent: 91.5:8.0:0.5 v/v/v dichloromethane-methanol-ammonia). After the solvents have been evaporated, the product thus obtained is crystallized from ethyl acetate. 4.95 g of 2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-N-methlbenzamide is obtained. Yield: 71%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04923865 |
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| Source dataset | uspto-grants-1990_05 |
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| ORD ID | ord-676ed8175a214f2ba52ab3ad4a88413f |
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| Source note | uspto-grants-1990_05 |
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