Sodium Hydroxide → HCID 15437529, compound

HRID 1870246Notes

Reaction equation

HRID 1870246 reaction equation
C([O:3][C:4]([CH:6]=[C:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:10][CH2:9][CH2:8]1)=[O:5])C.[OH-].[Na+]>CO>[C:4]([CH2:6][C:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)(=[O:19])=[O:20])[CH2:10][CH2:9][CH:8]=1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide3×HCID 541408341-(p-toluenesulfonyl)-5-ethoxycarbonylmethylidene-2,3,4,5-tetrahydro-1H-benzazepine

Product 1

HCID 15437529HCID 15437529, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A mixture of 5-ethoxycarbonylmethylidene-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (18.6 g), methanol (130 ml) and a 4N sodium hydroxide solution in methanol (9.7 ml) is refluxed for three hours. To the mixture is added a 4N sodium hydroxide solution in methanol (12 ml), and the mixture is refluxed for 4.5 hours. Further, to the mixture is added a 5N aqueous sodium hydroxide solution (9.7 ml), and the mixture is refluxed for one hour and concentrated. To residue are added water and ethyl acetate, and the mixture is acidified with conc. hydrochloric acid. The mixture is extracted with ethyl acetate. The organic layer is washed with water, and dried over magnesium sulfate, and concentrated. The residue is crystallized from diethyl ether--n-hexane, and recrystallized from methanol--water to give 5-carboxymethyl-2,3-dihydro-1-(p-toluenesulfonyl)-1H-benzazepine (17.1 g).

Workup

  1. temperaturethe mixture is refluxed for 4.5 hours
  2. temperaturethe mixture is refluxed for one hour
  3. concentrationconcentrated
  4. additionTo residue are added water and ethyl acetate
  5. extractionThe mixture is extracted with ethyl acetate
  6. washThe organic layer is washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue is crystallized from diethyl ether
  10. customn-hexane, and recrystallized from methanol

Sources & evidence

ORD record
ord-c05ec0b215f54a46bc01028d03fcea7d
Source dataset
uspto-grants-2000_08
Patent number
US06096736

Reaction notes

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