Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formamide | HCID 713 | — |
| Reactant | Ammonium formate | HCID 2723923 | — |
| Reactant | N-cyano-N'-[2-(2-formyloxy-3-oxobutylthio)ethyl]-N"-methylguanidine | HCID 14622764 | — |
| Reactant | Methylorthoformate | HCID 53629101 | — |
| Product | HCID 178484997 | HCID 178484997 | 56% |
Reaction Steps
136 mg of N-{2-(2-formyloxy-3-oxobutylthio)ethyl}-N'-cyano-N"-methylguanidine and 530 mg of methyl orthoformate were dissolved in 2.5 m; of formamide, and 320 mg of ammonium formate was added. The mixture was stirred at 100° C. for 2 hours. Formamide was evaporated from the reaction mixture under reduced pressure. The residue was chromatographed on a column of silica gel (eluent: chloroform/methanol=4/1), and then recrystallized from isopropanol to give 71 mg (yield 56%) of the desired product (Cimetidine) as white crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04894475 |
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| Source dataset | uspto-grants-1990_01 |
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| ORD ID | ord-b225c7d67cd84417b6419f7f2d2468fc |
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| Source note | uspto-grants-1990_01 |
|---|