Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Thiophosgene | HCID 10040 | — |
| Reactant | HCID 86606887 | HCID 86606887 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 60055571 | HCID 60055571 | 62% |
Reaction Steps
Thiophosgene (0.38 ml, 1.1 eq) is added dropwise to a solution cooled down to 0° C., of N-(4-aminophenyl)-N′-methoxyurea hydrochloride (1 g) and triethylamine (3.2 ml, 5 eq) in tetrahydrofuran (90 ml). The mixture is stirred for 15 min at 0° C. then water and diethyl ether are added. After decantation and extractions, the phases organic are combined, washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 7:3 to 3:7) produces the expected compound (630 mg; 62% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07355052B2 |
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| Source dataset | uspto-grants-2008_04 |
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| ORD ID | ord-d1a8c0367f4041ec82b776e4225ccedf |
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| Source note | uspto-grants-2008_04 |
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