Hydrochloric Acid → HCID 86699766, compound

HRID 515201Notes

Reaction equation

HRID 515201 reaction equation
[Cu][C:2]#[N:3].N(OC(C)(C)C)=O.[CH:11]([C:14]1[CH:19]=[C:18]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:17]=[C:16]([O:26][CH3:27])[C:15]=1N)([CH3:13])[CH3:12].Cl>CS(C)=O>[CH:11]([C:14]1[CH:19]=[C:18]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:17]=[C:16]([O:26][CH3:27])[C:15]=1[C:2]#[N:3])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 86699765HCID 86699765, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 86699766HCID 86699766, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
50 °C

Procedure

Copper(I) cyanide (1.07 g, 11.9 mmol) is added to dimethylsulfoxide (15 ml) at 50° C. followed by the addition of tert-Butyl nitrite (3.8 ml, 27.6 mmol) at once. A solution of (2-isopropyl-6-methoxy-4-morpholin-4-yl-phenyl)-amine (2.3 g, 9.2 mmol) in dimethylsulfoxide (15 ml) is added drop wise via an addition funnel to the above mixture. After completion of the addition, the reaction mixture is allowed to stir for 1 h at 50° C. After being cooled to 45° C., the reaction mixture is slowly treated with 5N hydrochloric acid and cooled to ambient temperature. The resulting mixture is extracted with ethyl acetate (3×50 ml). The combined organic layers are washed with water (30 ml), brine (30 ml), dried over sodium sulfate and evaporated to dryness. The crude product is purified by flash column chromatography (silica gel, 20% ethyl acetate/hexane) to afford 2-isopropyl-6-methoxy-4-morpholin-4-yl-benzonitrile (0.4 g, 1.54 mmol, 17%).

Workup

  1. additionAfter completion of the addition
  2. temperatureAfter being cooled to 45° C.
  3. temperaturecooled to ambient temperature
  4. extractionThe resulting mixture is extracted with ethyl acetate (3×50 ml)
  5. washThe combined organic layers are washed with water (30 ml), brine (30 ml)
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. customThe crude product is purified by flash column chromatography (silica gel, 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-463b9a4b489d4a71a5d51213e4032986
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

Loading…