HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethyl Sulfoxide → HCID 59424218, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethyl Sulfoxide | HCID 679 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | (2-m-tolyl-2H-tetrazol-5-yl)-methanol | HCID 59424221 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59424218 | HCID 59424218 | 64% |
Reaction Steps
A solution of oxalyl chloride (4.0 mL, 46 mmol) in CH2Cl2 (100 mL) at −78° C. was added DMSO (6.5 mL, 92 mmol) dropwise. The mixture was stirred for 10 minutes after which the title compound from Example 13.2 (7.92 mg, 41.6 mmol) in CH2Cl2 (30 mL) was added dropwise. The mixture was stirred for an additional 30 minutes and Et3N (2.9 mL, 208 mmol) was added dropwise. The reaction was then allowed to warm to room temperature. Water (150 mL) was then added and the organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (10-20% EtOAc/hexanes) to yield the title compound as an orange oil (4.98 g, 64%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07772235B2 |
| Source dataset | uspto-grants-2010_08 |
| ORD ID | ord-55f399fe3f5e4615ab7405b68af59cba |
| Source note | uspto-grants-2010_08 |