4-(3-thienyl)-8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine → HCID 178518636, compound

HRID 2257000Notes

Reaction equation

HRID 2257000 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:7](=[O:21])[C:8]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:9]=3[NH:10][C:11](=[O:15])[C:12]=2[O:13]C)=[CH:2]1>Cl.C1COCC1>[Cl:20][C:17]1[CH:18]=[CH:19][C:8]2[C:7](=[O:21])[C:6]([C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)=[C:12]([OH:13])[C:11](=[O:15])[NH:10][C:9]=2[CH:16]=1

Participants

3

Reactant 1

HCID 189800404-(3-thienyl)-8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine

Product 1

HCID 178518636HCID 178518636, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 18422008HCl tetrahydrofuranSolvent

Procedure

A solution of 4-(3-thienyl)-8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.74 g) in 2.4N HCl/THF (1:1, 600 mL) was allowed to stir at room temperature for 48 hours. The reaction mixture was partitioned between ether and water. The organic portion was dried (MgSO4), filtered, and concentrated in vacuo. The residue was recrystallized twice from ethyl acetate/hexanes (2:1) to afford the title compound (0.173 g); mp 248° C. (dec.); NMR: 11.75 (bs, 1), 10.45 (bs, 1), 7.80 (d, 1, J=8.6), 7.64 (m, 1), 7.48 (m, 2), 7.33 (dd, 1, J=8.6, 2.0), 7.15 (dd, 1, J=5.0, 1.2). Analysis for C14H8O3NSCl: Calculated: C, 55.00; H, 2.64; N, 4.58; Found C, 54.77; H, 2.81; N, 4.56

Workup

  1. customThe reaction mixture was partitioned between ether and water
  2. dry with materialThe organic portion was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized twice from ethyl acetate/hexanes (2:1)

Sources & evidence

ORD record
ord-4440e77ff5e54d3fbb7f71b78c5ff14d
Source dataset
uspto-grants-1997_08
Patent number
US05656626

Reaction notes

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