Dimethylamine → HCID 19704913, compound

HRID 2396473Notes

Reaction equation

HRID 2396473 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]([CH3:13])=[C:9](OC)[C:8](=[O:16])[NH:7][C:6]=2[CH:17]=1.[CH3:18][NH:19][CH3:20]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]([CH3:13])=[C:9]([N:19]([CH3:20])[CH3:18])[C:8](=[O:16])[NH:7][C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 19704904HCID 19704904, compound

Product 1

HCID 19704913HCID 19704913, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

8-Chloro-3-methoxy-4-methyl-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.4 g) was treated with 100 mL of liquid dimethylamine chilled to -78° C. The mixture was sealed in a pressure vessel and warmed to 26° C. for 72 hours. The excess dimethylamine was evaporated to give an oil which was dissolved in water and extracted with ethyl acetate. The organic extracts were combined and concentrated to a brown oil. The oil was crystallized using ether to give a yellow solid. The solid was purified by chromatography, with ethyl acetate:hexane (1:1) as the eluent, to give the title compound; NMR: 2.95 (s,6), 2.28 (s,3); MS: m/z=265(M+1).

Workup

  1. customThe mixture was sealed in a pressure vessel
  2. temperaturewarmed to 26° C. for 72 hours
  3. customThe excess dimethylamine was evaporated
  4. customto give an oil which
  5. extractionextracted with ethyl acetate
  6. concentrationconcentrated to a brown oil
  7. customThe oil was crystallized
  8. customto give a yellow solid
  9. customThe solid was purified by chromatography, with ethyl acetate:hexane (1:1) as the eluent

Sources & evidence

ORD record
ord-39e2f1142e374f05982ffbfa75868abb
Source dataset
uspto-grants-1996_02
Patent number
US05492905

Reaction notes

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