Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzene, 1-chloro-3-isocyanato- | HCID 17968 | — |
| Reactant | HCID 376124 | HCID 376124 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 18930594 | HCID 18930594 | 87.7% |
Reaction Steps
A solution of m-chlorophenylisocyanate (756 mg, 4.92 mmol) in tetrahydrofuran (8 ml) is added to a solution of the salt 3a (1.341 g, 4 mmol) prepared in Preparation 3 in tetrahydrofuran (50 ml). Triethylamine (1.67 μl, 12 mmol) is added at 0 ° C., and the mixture is stirred at 0° C. for 30 minutes and then at room temperature overnight. Water and then 10% hydrochloric acid are added, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried (sodium sulfate), and distilled under reduced pressure to remove the solvent. The residue is recrystallized from dichloromethane/diisopropylalcohol to obtain the objective compound 6u (1.43 g; yield 73%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05739162 |
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| Source dataset | uspto-grants-1998_04 |
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| ORD ID | ord-79514dc844c4459a9a874256f728cb47 |
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| Source note | uspto-grants-1998_04 |
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