HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → [1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-1H-imidazol-4-yl]-methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Ethyl orthoformate | HCID 31214 | — |
| Reactant | Ethyl nitroacetate | HCID 69379 | — |
| Reactant | 5-Amino-2,2-difluoro-1,3-benzodioxole | HCID 2736893 | — |
| Catalyst | Iron | HCID 23925 | — |
| Product | [1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-1H-imidazol-4-yl]-methanol | HCID 23445088 | — |
Reaction Steps
Following the general method described in example 293, 2,2-difluoro-benzo[1,3]dioxol-5-ylamine was reacted with triethyl orthoformate, ethyl nitroacetate and acetic acid followed by treatment with triethyl orthoformate, iron and acetic acid and subsequent alkaline hydrolysis. The isolated acid was directly reduced according to example 264, by reaction with BH3 THF complex followed by hydrolytic workup and the title compound was obtained as a light brown solid. Mp. 163-164° C. (H2O), MS: m/e=254 (M+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06667335B2 |
| Source dataset | uspto-grants-2003_12 |
| ORD ID | ord-2ac297953db6476b92c7922ceb60d9f8 |
| Source note | uspto-grants-2003_12 |