Sulfuric Acid → Ethyl 2-(2,3-dioxo-4,5-dihydro-1-benzazepin-1-yl)acetate

HRID 647887Notes

Reaction equation

HRID 647887 reaction equation
N1CC[O:4]CC1.Cl[C:8]1(Cl)[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[N:10]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:9]1=[O:25].OS(O)(=O)=O>C(Cl)(Cl)Cl>[CH2:23]([O:22][C:20]([CH2:19][N:10]1[C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[CH2:13][CH2:14][C:8](=[O:4])[C:9]1=[O:25])=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8083MorpholineHCID 154880513,3-dichloro-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one

Product 1

HCID 13500724Ethyl 2-(2,3-dioxo-4,5-dihydro-1-benzazepin-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of morpholine (0.315 ml, 3.6 mmol) and 3,3-dichloro-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (0.5 g) was stirred under nitrogen at 110° for 18 hours. The solution was diluted to 10 ml with chloroform and cooled to 0°. 20% H2SO4 (1 ml) was added and the solution stirred for 2 hours at 0°. The solution was extracted with chloroform (2×20 ml) and the extracts washed with 2N HCl (2×10 ml) and saturated brine (5 ml). The solution was dried over magnesium sulfate and evaporated under reduced pressure to yield 1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2,3- dione. NMR (CDCl3): δ1.25 (t,3H); 2.6 (m,2H); 3.6 (m, 2H); 4.2 (q, 2H); 7.3 (m, 4H).

Workup

  1. temperaturecooled to 0°
  2. stirringthe solution stirred for 2 hours at 0°
  3. extractionThe solution was extracted with chloroform (2×20 ml)
  4. washthe extracts washed with 2N HCl (2×10 ml) and saturated brine (5 ml)
  5. dry with materialThe solution was dried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9054d9c489f1420989a7934b7ed1e7e7
Source dataset
uspto-grants-1983_10
Patent number
US04410520

Reaction notes

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