Hydrochloric Acid → HCID 59845677, compound

Temperature

0 °C

5-Chloro-2-methylsulfanyl-benzonitrile (3.9 g, 21.2 mmol) was dissolved in THF (42 mL) and cooled to 0 degrees C. Borane-THF complex (50 mL of a 1M THF solution) was added dropwise. After 10 minutes at 0 degrees C. the reaction was warmed to 65 degrees C. for 4 h. Methanol (approximately 30 mL) was added to the reaction at 0 degrees C. The reaction was warmed to room temperature and stirred for 10 minutes. The reaction solution was concentrated in-vacuo to yield a thick oil which was dissolved in 50% THF/MeOH (30 mL). 4M HCl (30 mL) was added slowly. After 10 minutes, the solution was partitioned between water (10 mL) and DCM (20 mL). The aqueous layer was extracted with DCM (30 mL) and the organic layers were discarded. The aqueous layer was neutralized to pH9 with 5M NaOH. The solution was extracted with DCM (3×70 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to yield 2.9 g of 5-chloro-2-methylsulfanyl-benzylamine as a pale yellow oil, 1H NMR 400 MHz (CDCl3) δ 7.33 (d, 1H, J=2.4 Hz), 7.22 (dd, 1H, J=2.4, 8.4 Hz), 7.13 (d, 1H, J=5 8.4 Hz), 3.89 (s, 2H), 2.48 (s, 3H).

1. temperaturethe reaction was warmed to 65 degrees C
2. waitfor 4 h
3. temperatureThe reaction was warmed to room temperature
4. concentrationThe reaction solution was concentrated in-vacuo
5. customto yield a thick oil which
6. waitAfter 10 minutes
7. customthe solution was partitioned between water (10 mL) and DCM (20 mL)
8. extractionThe aqueous layer was extracted with DCM (30 mL)
9. extractionThe solution was extracted with DCM (3×70 mL)
10. washThe combined organic layers were washed with brine
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. concentrationconcentrated

ORD record

ord-ba869a0636644a0fbb8d689f111c7fb1

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601714B2