Diisopropylethylamine → HCID 14098489, compound

HRID 1194261Notes

Reaction equation

HRID 1194261 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[S:12])[C:7]2[CH:13]=[CH:14][CH:15]=[N:16][C:6]=2[O:5]1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH:27][CH3:28])=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C>C(O)C>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][N:27]([CH3:28])[CH2:2][CH2:3][CH:4]2[CH2:10][N:9]([CH3:11])[C:8](=[S:12])[C:7]3[CH:13]=[CH:14][CH:15]=[N:16][C:6]=3[O:5]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1047354-Methoxy-N-methylbenzeneethanamine2×HCID 137264422-(chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)thione

Product 1

HCID 14098489HCID 14098489, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 40 ml of absolute ethanol was added 5.0 g (0.0195 mole) of 2-(2-chloroethyl-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione and 3.65 g (0.022 mole) of 4-methoxy-N-methylbenzene-ethanamine and 2.5 g (0.0195 mole) of diisopropylethylamine. After ~6 hr heating at reflux 3.15 g (0.022 mole) of 4-methoxy-N-methylbenzeneethanamine was added and heating was continued overnight. After removing the solvent by rotary evaporation, the residue was taken up in 100 ml of methylene chloride and the solution was washed with 2×50 ml of 1N sodium hydroxide and 50 ml of water, dried over sodium sulfate and filtered. The solution was then treated with 10 ml of acetic anhydride overnight. The methylene chloride was extracted with 3×100 ml of hydrochloric acid. The combined aqueous extracts were washed with 2×100 ml of chloroform made basic with concentrated sodium hydroxide and extracted into 3×100 ml of chloroform. The organic layer was dried over sodium sulfate, filtered, and concentrated by rotary evaporation to give 2.8 g (37%) of yellow, analytically pure crystals, m.p. 75°-78° C.

Workup

  1. temperatureAfter ~6 hr heating
  2. additionwas added
  3. temperatureheating
  4. customAfter removing the solvent
  5. customby rotary evaporation
  6. washthe solution was washed with 2×50 ml of 1N sodium hydroxide and 50 ml of water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. additionThe solution was then treated with 10 ml of acetic anhydride overnight
  10. extractionThe methylene chloride was extracted with 3×100 ml of hydrochloric acid
  11. washThe combined aqueous extracts were washed with 2×100 ml of chloroform
  12. extractionextracted into 3×100 ml of chloroform
  13. dry with materialThe organic layer was dried over sodium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated by rotary evaporation
  16. customto give 2.8 g (37%) of yellow, analytically pure crystals, m.p. 75°-78° C.

Sources & evidence

ORD record
ord-05f87ddb66004cbe86e44f8dbd05c2c2
Source dataset
uspto-grants-1989_03
Patent number
US04812565

Reaction notes

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