4-(2-thienyl)-8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine → HCID 178518635, compound

HRID 2256999Notes

Reaction equation

HRID 2256999 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:7](=[O:21])[C:8]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:9]=2[NH:10][C:11](=[O:15])[C:12]=1[O:13]C>Cl.C1COCC1>[Cl:20][C:17]1[CH:18]=[CH:19][C:8]2[C:7](=[O:21])[C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[C:12]([OH:13])[C:11](=[O:15])[NH:10][C:9]=2[CH:16]=1

Participants

3

Reactant 1

HCID 189800434-(2-thienyl)-8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine

Product 1

HCID 178518635HCID 178518635, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 18422008HCl tetrahydrofuranSolvent

Procedure

A solution of 4-(2-thienyl)-8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.20 g) in 2.4N HCl/THF (1:1, 200 mL) was allowed to stir at room temperature for 1 hour followed by heating to 50° C. for 1 hour. 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 to afford the title compound (0.048 g); mp 231°-233° C. (dec.); NMR: 11.70 (bs, 1), 7.72 (d, 1, J=8.6), 7.62-7.60 (m,2), 7.40 (d, 1, J=1.9), 7.32 (dd, 1, J=8.6, 2.0), 7.10 (m, 1). Analysis for C14H8O3NClS 0.25 H2O.: Calculated: C, 54.29; H, 2.76; N, 4.51; Found C, 54.38; H, 2.90; N, 4.41.

Workup

  1. temperatureby heating to 50° C. for 1 hour
  2. customThe reaction mixture was partitioned between ether and water
  3. dry with materialThe organic portion was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized twice from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5ed356c1b0964d10817e58494d1fa2c9
Source dataset
uspto-grants-1997_08
Patent number
US05656626

Reaction notes

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