Ethanol → HCID 19760210, compound

HRID 1586922Notes

Reaction equation

HRID 1586922 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[C:10]([NH:13][C:14]([C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][CH:17]=3)=[O:15])[CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][CH2:4][C:3]1=[O:27].C(O)C.[OH-].[Na+]>O1CCCC1>[CH3:1][N:2]1[C:8]2[CH:9]=[C:10]([NH:13][C:14]([C:16]3[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:25][CH:26]=3)=[O:15])[CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][CH2:4][C:3]1=[O:27]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 19760213HCID 19760213, compound

Product 1

HCID 19760210HCID 19760210, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

850 mg of ethyl p-[(2,3,4,5-tetrahydro-1-methyl-2-oxo-1H-1-benzazepine-8-yl)carbamoyl]benzoate were dissolved in 20 ml of tetrahydrofuran and 10 ml of ethanol and treated with 10 ml of 1.2N NaOH yielding a two-phase mixture. The mixture was stirred intensively at 35° C. for 8 hours, poured into an ice/conc. HCl solution and extracted thoroughly with ethyl acetate. The resulting product was washed with a small amount of NaCl solution, dryed, and concentrated, and the remaining residue was repeatedly boiled in ethyl acetate and dryed yielding 400 mg of p-[(2,3,4,5-tetrahydro-1-methyl-2-oxo-1H-1-benzazepin-8-yl)carbamoyl]benzoic acid as beige crystals, m.p. >270° C.

Workup

  1. extractionHCl solution and extracted thoroughly with ethyl acetate
  2. washThe resulting product was washed with a small amount of NaCl solution
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cefb62e414bf4a4abb4877dcc69174ba
Source dataset
uspto-grants-1993_06
Patent number
US05216148

Reaction notes

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