Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 89560616 | HCID 89560616 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 89560543 | HCID 89560543 | 99% |
Reaction Steps
To a solution of 3-(3-hydroxypropyl)-2-oxo-2,3-dihydro-1,3-benzothiazole-6-carbaldehyde (Intermediate 71, 158 mg, 0.67 mmol) in CH2Cl2 (5 mL) was added Et3N (0.11 mL, 0.80 mmol) and the mixture was cooled to 0° C. To this solution, methanesulfonyl chloride was added dropwise (57 μL, 0.74 mmol) and the mixture was maintained at 0° C. for 90 min. CH2Cl2 and 4% aqueous sodium bicarbonate solution (10 mL) were added to the reaction mixture and stirred for 10 min. The two layers were separated and the organic phase was washed with water and brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to give the title compound as a colourless oil (243 mg, 99% yield) which was used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09233108B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-d96b328fddf44cf1b466cef56bd14134 |
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| Source note | uspto-grants-2016_01 |
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