Triethylamine → HCID 14974919, compound

HRID 1441125Notes

Reaction equation

HRID 1441125 reaction equation
CO[C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6](=[O:11])[C:5](=[O:12])[CH:4]=1.Cl.[Cl:14][CH2:15][CH2:16][NH2:17].C(N(CC)CC)C>ClCCl>[Cl:14][CH2:15][CH2:16][NH:17][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6](=[O:11])[C:5](=[O:12])[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 887864,5-Dimethoxy-o-benzoquinoneHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 14974919HCID 14974919, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4,5-Dimethoxy-1,2-benzoquinone (672.4 mg, 4 mmol) was dissolved in dichloromethane (40 ml) and stirred in a round-bottomed flask equipped with a cylindrical funnel from which a solution of chloroethylamine hydrochloride (1.2 g, 4.4 mmol) and triethylamine (2.4 ml, 16.8 mmol) in dichloromethane (50 ml) was added dropwise into the solution over the course of one hour. The reaction mixture was maintained with stirring at room temperature for 21 hours. After filtration, the remaining solution was washed with 10% hydrochloric acid, distilled water and then distilled water saturated with sodium chloride, and then dried over magnesium sulfate. Evaporation of the solvent gave the black red crude product. Column chromatography with chloroform: methanol (4:0.5, (v/v)) elution gave 4-chloroethylamino-5-methoxy-1,2-benzoquinone 274.3 mg, 31.8% yield) which was recrystallized from ethanol as red needles: mp 150°-152° C.; Found: C,50.17; H,4.77; N,6.44; Cl,16.39. Anal. Calcd. for C9H10ClNO3 : C,50.13; H,4.67; N,6.49; Cl,16.44%. I.R. υmax 3400, 2940, 1660, 1640, 1620, 1580, 1510, 1250, 1180, 810 cm-1. U.V. λmax (95% EtOH) 210 nm (log ε4.35), 304 (4.23), 464 (3.51), 1HNMR (CDCl3) δ, 3.6 (m, 4H, NCH2CH2), 3.9 (S, 3H, O CH3), 5.4 (S, 1H, 6-H), 5.7 (s, 1H, 3-H), 6.2 (br,s, 1H, NH).

Workup

  1. additionwas added dropwise into the solution over the course of one hour
  2. temperatureThe reaction mixture was maintained
  3. stirringwith stirring at room temperature for 21 hours
  4. filtrationAfter filtration
  5. washthe remaining solution was washed with 10% hydrochloric acid
  6. distillationdistilled water
  7. dry with materialdistilled water saturated with sodium chloride, and then dried over magnesium sulfate
  8. customEvaporation of the solvent
  9. customgave the black red crude product
  10. washColumn chromatography with chloroform: methanol (4:0.5, (v/v)) elution

Sources & evidence

ORD record
ord-ac708f31718246ceb97f9600c9996d8a
Source dataset
uspto-grants-1996_03
Patent number
US05502214

Reaction notes

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