Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Glycine | HCID 750 | — |
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 2-(Chloromethyl)benzoyl chloride | HCID 3016395 | — |
| Reactant | 2-azidobenzaldehyde | HCID 10888060 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 123709625 | HCID 123709625 | — |
Reaction Steps
Glycine (3 g) was dissolved in a mixture of water (20 g), acetonitrile (10 g), and sodium hydroxide (2 g), and the solution was cooled to 10° C., to thereby prepare a glycine solution. Separately, chloromethylbenzoyl chloride (8 g) was dissolved in acetonitrile (20 g), and the solution was cooled to 10° C. The liquid was added dropwise to the glycine solution over 2 hours. Simultaneously, a solution of sodium hydroxide (2 g) dissolved in water (20 g) was added to the glycine solution over 2 hours. Five hours later, morpholine (4 g) was added thereto, and the mixture was allowed to react at 60° C. for 4 hours, followed by cooling the resultant solution to 10° C. Triethylamine (4 g) was further added, and then ethyl chloroformate (4.5 g) was added dropwise thereto over 30 minutes. The resultant mixture was continuously stirred for 2 hours. Subsequently, azidobenzaldehyde (3.5 g) was added, and the mixture was allowed to react at 20° C. for 16 hours. The thus-formed precipitates were separated through filtration and dried, to thereby yield 1 g of photosensitive material G as a target compound. Photosensitive material G was dissolved in acetonitrile, and a UV absorption spectrum of the solution was measured, and an absorption peak attributed to an azlactone ring was identified at 387 nm. FIG. 3 illustrates the UV absorption spectrum of photosensitive material G.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09223210B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-9c0c837c32414ee49a6072ccf8887e28 |
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| Source note | uspto-grants-2015_12 |
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