Propylamine → HCID 86662067, compound

HRID 2283219Notes

Reaction equation

HRID 2283219 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:5]([C:6]([O:8]C)=O)=[C:4]([N+:13]([O-:15])=[O:14])[C:3]=1[O:16][CH3:17].[CH2:18]([NH2:21])[CH2:19][CH3:20]>S(Cl)(Cl)=O>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:5]([C:6]([NH:21][CH2:18][CH2:19][CH3:20])=[O:8])=[C:4]([N+:13]([O-:15])=[O:14])[C:3]=1[O:16][CH3:17]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 59726037HCID 59726037, compound

Product 1

HCID 86662067HCID 86662067, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

The acid 2-2 (1.41 g, 5.3 mmol) was heated to reflux in thionyl chloride (20 mL) for 2 h. After cooling, the volatiles were removed in vacuo and the residue was azeotroped with toluene. The resulting acid chloride was dried at high vacuum and then dissolved in anhydrous CH2Cl2 (50 mL), cooled to 0° C. then treated with propylamine (2.45 mL, 29.9 mmol). The reaction was warmed to room temperature for 2 h. The solvent was removed in vacuo and the residue was taken up in EtOAc and brine. The aqueous layer was extracted three times into EtOAc and the combined organic layers were washed with H2O, dried over Na2SO4, filtered and concentrated to provide the amide in which R is propyl 4-5 as a light orange solid. (1.5 g, 92% yield). 1H NMR (400 MHz, d6-DMSO) δ 0.91 (t, J=7.0 Hz, 3H), 1.40 (q, J=7.0 Hz, 2H), 3.07 (q, J=7.0 Hz, 2H), 3.84 (s, 3H), 8.13 (s, 1H), 8.84 (br s, 1H).

Workup

  1. temperatureAfter cooling
  2. customthe volatiles were removed in vacuo
  3. customthe residue was azeotroped with toluene
  4. dry with materialThe resulting acid chloride was dried at high vacuum
  5. dissolutiondissolved in anhydrous CH2Cl2 (50 mL)
  6. temperatureThe reaction was warmed to room temperature for 2 h
  7. customThe solvent was removed in vacuo
  8. extractionThe aqueous layer was extracted three times into EtOAc
  9. washthe combined organic layers were washed with H2O
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-3afe628815cb434595bca68cb52418a7
Source dataset
uspto-grants-2015_09
Patent number
US09145375B2

Reaction notes

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