Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Cyclopropanecarbonyl chloride | HCID 77637 | — |
| Reactant | 1-(5-Amino-3-bromo-1,2-thiazol-4-yl)ethan-1-one | HCID 12246192 | — |
| Product | HCID 66838440 | HCID 66838440 | 60% |
Reaction Steps
Add triethylamine (234.5; mL, 1.68; mol) to a cooled suspension of 1-(5-amino-3-bromo-isothiazol-4-yl)-ethanone (310; g, 1.40; mol) in dichloromethane (2.79; L, 43.53 mol) at 0° C. under nitrogen and then add slowly a solution of cyclopropanecarbonyl chloride (137.5; mL, 1.47; mol) in dichloromethane (310; mL, 4.84; mol) at 0° C. over 1 hour. Warm to 16° C. over 2; hours and then cool to 10° C., add water (1; L) and separate the layers. Extract the aqueous layer once with dichloromethane (500; mL). Combine the organic layers, concentrate and purify by silica gel chromatography eluting with n-hexane:dichloromethane 30:70. Triturate the recovered solid with hexanes to give the title compound as a white solid (256.1; g, 60%). MS (m/z): 289, 291; (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07932274B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-548adc55b3a44913b7f14b0aa91d1731 |
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| Source note | uspto-grants-2011_04 |
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