Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | 1,2-Dimethoxyethane | HCID 8071 | — |
| Reactant | Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamate | HCID 98708 | — |
| Reactant | 4-Bromobenzene-1,2-diamine | HCID 323593 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | NSC154754 | HCID 290654 | 77.4% |
Reaction Steps
To a slurry of 4-bromobenzene-1,2-diamine (2.1 g, 11 mmol), 1,2-dimethoxyethane (20 mL) and methanol (5 mL) was added 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (4.0 g, 19 mmol). The reaction mixture was heated (105° C.) for 12 h and then diluted with ethyl ether (100 mL). The resulting precipitate was collected by filtration and rinsed with ethyl ether (2×25 mL) to provide methyl 6-bromo-1H-benzo[d]imidazol-2-ylcarbamate (2.3 g, 77% yield). MS (EI) for C9H8BrN3O2: 271 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08637499B2 |
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| Source dataset | uspto-grants-2014_01 |
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| ORD ID | ord-78286d968da94b96a4191904bb91bcd0 |
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| Source note | uspto-grants-2014_01 |
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