Phenethylamine → 8-Chloro-2,5-dioxo-3-phenethylamino-2,5-dihydro-1H-benz[b]azepine

HRID 2396463Notes

Reaction equation

HRID 2396463 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH:10]=[C:9](OC)[C:8](=[O:15])[NH:7][C:6]=2[CH:16]=1.[CH2:17]([NH2:25])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH:10]=[C:9]([NH:25][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:8](=[O:15])[NH:7][C:6]=2[CH:16]=1

Participants

3

Reactant 2

HCID 1001PhenethylamineHCID 150296358-Chloro-3-methoxy-1H-1-benzazepine-2,5-dione

Product 1

HCID 197048998-Chloro-2,5-dioxo-3-phenethylamino-2,5-dihydro-1H-benz[b]azepine

Conditions

Temperature
80 °C

Procedure

8-Chloro-3-methoxy-2,5-dioxo-2,5-dihydro1H-benz[b]azepine (0.5 g) was treated with 5 mL of phenethylamine, and the mixture was heated to 80° C. for 1 hour. The reaction mixture was filtered and the solid recrystallized from 5 mL hot dimethylformamide and water. The solid was filtered, washed (water) and vacuum dried (100° C., 15 Pa) to give the title compound (0.329 g); mp 284.4-286.9° C.; NMR: 5.89 (s,1): MS: m/z=327(M+1). Analysis for C18H15ClN2O2 ·0.2 H2O: Calculated: C, 65.44; H, 4.70; N, 8.48; Found: C, 65.42; H, 4.72; N, 8.62.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solid recrystallized from 5 mL hot dimethylformamide and water
  3. filtrationThe solid was filtered
  4. washwashed (water) and vacuum
  5. customdried (100° C., 15 Pa)

Sources & evidence

ORD record
ord-e596d15aefd44c44b5806c7bb4eb088b
Source dataset
uspto-grants-1996_02
Patent number
US05492905

Reaction notes

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