Benzylamine → 3-Benzylamino-8-chloro-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine

HRID 2396464Notes

Reaction equation

HRID 2396464 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]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[CH2:17]([NH:24][C:9]1[C:8](=[O:15])[NH:7][C:6]2[CH:16]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[C:11](=[O:12])[CH:10]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 150296358-Chloro-3-methoxy-1H-1-benzazepine-2,5-dione

Product 1

HCID 197049163-Benzylamino-8-chloro-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.5 g) in methanol (15 mL) was added benzylamine (0.3 mL). The mixture was heated to reflux for 24 hours. The solvent was evaporated to give a solid. The solid was recrystallized from dimethylformamide (5 mL) and water, washed (water) and vacuum dried (100° C., 15 Pa) to give the title compound (0.181 g); mp 309.1°-313.9° C.; NMR: 5.73 (s,1); MS: m/z=313(M+1). Analysis for C17H13ClN2O2 : Calculated: C, 65.29; H, 4.19; N, 8.96; Found: C, 65.02; H, 3.96; N, 8.61.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 hours
  3. customThe solvent was evaporated
  4. customto give a solid
  5. customThe solid was recrystallized from dimethylformamide (5 mL) and water
  6. washwashed (water) and vacuum
  7. customdried (100° C., 15 Pa)

Sources & evidence

ORD record
ord-79360eabefcf44c3a430a9537fc08173
Source dataset
uspto-grants-1996_02
Patent number
US05492905

Reaction notes

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