Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | 2-Methoxyethyl chloroformate | HCID 69400 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 18948816 | HCID 18948816 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86605583 | HCID 86605583 | 63% |
Reaction Steps
To a solution of 4-[[2-(dimethylamino)ethyl]amino]benzaldehyde (300 mg) in methylene chloride (4 mL) is added 2-methoxyethyl chloroformate (234 μL) and thereto is added dropwise pyridine (252 μL) under ice-cooling. The mixture is stirred at 50° C. for 2 days. The reaction mixture is diluted with chloroform (5 mL) and thereto is added a saturated sodium hydrogencarbonate solution (10 mL). After stirring, the organic layer is separated and concentrated. The residue is purified by column chromatography on silica gel (Solvent; chloroform:methanol=100:0→90:10) to give 4-[N-[(2-methoxyethoxy)carbonyl]-N-[2-(dimethylamino)ethyl]amino]benzaldehyde (290 mg, yield; 63%) as an amorphous powder. MS (APCI) m/z: 294 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07384952B2 |
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| Source dataset | uspto-grants-2008_06 |
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| ORD ID | ord-e799903fc09548ef96dcda08f1876ff3 |
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| Source note | uspto-grants-2008_06 |
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