Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzaldehyde | HCID 240 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 3-Amino-5-(3,5-dichloroanilino)-s-triazole | HCID 72714614 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 178478185 | HCID 178478185 | 98% |
Reaction Steps
A solution of N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 2 (70 mg, 287 μmol) and benzaldehyde (121.3 mg, 1.14 mmol) in MeOH (3 ml) was stirred at 45° C. for 2 days to give a suspension, cooled to −20° C. and was filtered to collect the solid. The solid was re-suspended in MeOH (5 ml), NaBH4 (65.1 mg, 1.72 mmol) was added and the reaction was stirred for 1 hour. The solvent was removed, and the reaction mixture was redissolved in EtOAc (5 ml) and washed with water (2×4 ml), dried over MgSO4 and concentrated in vacuo. Crystallization from DCM afforded a white solid as desired product (94 mg, 98% yield). MS +m/z: 334 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09428469B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-a662fcda1e11437b833c5403411f73f2 |
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| Source note | uspto-grants-2016_08 |
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