Hydrochloric Acid → HCID 57448161, compound

HRID 1667576Notes

Reaction equation

HRID 1667576 reaction equation
[CH:1]1([S:4][C:5]2[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=2[C:7]#[N:8])[CH2:3][CH2:2]1.S(C)C.[ClH:16]>C1COCC1>[ClH:16].[CH:1]1([S:4][C:5]2[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=2[CH2:7][NH2:8])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1068Dimethyl SulfideHCID 574481602-(Cyclopropylsulfanyl)benzonitrile

Product 1

HCID 57448161HCID 57448161, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1A (1.50 g, 7.25 mmol) in refluxing THF (72 mL) was added a 2M THF solution of BH3.SMe2 (10.8 mL, 21.7 mmol). After heating at reflux for 2 h, the reaction was cooled to rt and 6M HCl (4.32 mL) was slowly added. The reaction was heated to reflux for 30 min, then cooled to rt, concentrated and azeotroped (3×) with THF/MeOH on a rotary evaporator. The resulting residue was taken up in THF and filtered to provide 1B (1.40 g, 79%) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 1.15 (m, 2H) 1.29 (m, 2H) 2.91 (m, 1H) 4.52 (s, 2H) 7.72 (m, J=7.69, 7.69 Hz, 2H) 7.80 (t, J=6.81 Hz, 1H) 8.04 (d, J=7.91 Hz, 1H).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2 h
  3. temperatureThe reaction was heated
  4. temperatureto reflux for 30 min
  5. temperaturecooled to rt
  6. concentrationconcentrated
  7. customazeotroped (3×) with THF/MeOH
  8. customon a rotary evaporator
  9. filtrationfiltered

Sources & evidence

ORD record
ord-98c0fe9cac714b6d91868400869e3df4
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

Loading…