Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | HCID 59591433 | HCID 59591433 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59591443 | HCID 59591443 | 71% |
Reaction Steps
To an ice cold solution of DMF (0.20 ml) and acetonotrile (5 ml) was added oxalyl chloride (45 μL, 0.52 mmol) dropwise while maintaining the temperature to 0° C. The reaction mixture was stirred at 0° C. for 40 min followed by addition of a solution of 3-((4-bromothiazol-2-yl)methoxy)-2,6-difluorobenzamide (0.15 g, 0.43 mmol) in DMF (2 ml). The resulting reaction mixture was stirred at 0° C. 40 min and then allowed to come to room temperature. After completion of reaction (10 min, TLC monitoring), triethyl amine (100 μL, 0.86 mmol) was added dropwise. The reaction mass was concentrated in vaccuo followed by addition of water (50 ml) and extraction with ethyl acetate (3×75 ml). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified over silica gel (60-120 M, 20% EtOAc-Hexane) to get the desired product (0.10 g, 71%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08415383B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-4794126c560544f1a5fa4edffbc23c7b |
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| Source note | uspto-grants-2013_04 |
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