Hydrochloric Acid → HCID 22311124, compound

3-(tert-Butyl)aniline (0.054 g, 0.36 mmol) was dissolved in ethyl acetate (2 mL) and added dry hydrogen chloride in ethyl acetate twice (3.5 M, 3 mL+2.5 mL). After 15 min the mixture was concentrated to dryness and co-evaporated three times from toluene (3×5 mL). The residue was added toluene (2.5 mL) and flushed with nitrogen for about 10 min, before diphosgene (0.43 mL) was added. Then the mixture was gently refluxed for 1 hour under a nitrogen atmosphere. The mixture was cooled and concentrated in vacuo. This was repeated twice to remove excess of diphosgene. The mixture was concentrated to dryness and coevaporated three times from toluene (5 mL each time). The residue was concentrated to dryness and co-evaporated twice from toluene. Then it was redissolved in toluene (2.5 mL) and flushed with nitrogen for about 10 min, before diphosgene (0.43 mL) was added. The mixture was gently refluxed under nitrogen for 1 hour. After cooling, the mixture was concentrated and co-evaporated twice from toluene to remove excess diphosgene to afford 3-tert-butyl-phenyl isocyanate.

1. concentrationAfter 15 min the mixture was concentrated to dryness and co-evaporated three times from toluene (3×5 mL)
2. additionThe residue was added toluene (2.5 mL)
3. customflushed with nitrogen for about 10 min, before diphosgene (0.43 mL)
4. additionwas added
5. temperatureThen the mixture was gently refluxed for 1 hour under a nitrogen atmosphere
6. temperatureThe mixture was cooled
7. concentrationconcentrated in vacuo
8. customto remove excess of diphosgene
9. concentrationThe mixture was concentrated to dryness
10. concentrationThe residue was concentrated to dryness
11. dissolutionThen it was redissolved in toluene (2.5 mL)
12. customflushed with nitrogen for about 10 min, before diphosgene (0.43 mL)
13. additionwas added
14. temperatureThe mixture was gently refluxed under nitrogen for 1 hour
15. temperatureAfter cooling
16. concentrationthe mixture was concentrated and co-evaporated twice from toluene
17. customto remove excess diphosgene

ORD record

ord-8315f489ae524563b5bb2e298e8d3f5c

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06562807B2