Potassium Carbonate → HCID 14855985, compound

HRID 1032638Notes

Reaction equation

HRID 1032638 reaction equation
C([O:4][C@H:5]1[C@@H:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[S:10][C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:8]([CH3:26])[N:7]([CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[C:6]1=[O:32])(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:4][C@H:5]1[C@@H:11]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[S:10][C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:8]([CH3:26])[N:7]([CH2:27][CH2:28][N:29]([CH3:30])[CH3:31])[C:6]1=[O:32]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 14855982HCID 14855982, compound

Product 1

HCID 14855985HCID 14855985, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.5 g (0.0033 mol) of cis-rac.-6-(acetyloxy)-6,7-dihydro-7-(4-methoxyphenyl)-3-methyl-4-[2-(dimethylamino)ethyl]-2-phenyl-1,4-thiazepin-5(4H)-one in 36 ml of ethanol was added 24 ml of 0.5 M potassium carbonate. After the reaction was heated for 1 hour at 70°-80°, it was concentrated to a low volume and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4) and the solvent was removed under reduced pressure. The residue was crystallized from ether to give 0.9 g (67%) of cis-rac.-6-(hydroxy)-6,7-dihydro-7-(4-methoxyphenyl)-3-methyl-4-[2(dimethylamino)ethyl]-2-phenyl-1,4-thiazepin-5(4H)-one, mp 110°-111°.

Workup

  1. temperatureAfter the reaction was heated for 1 hour at 70°-80°
  2. concentrationit was concentrated to a low volume
  3. extractionextracted with ethyl acetate
  4. washThe organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-7633b4bf532344af82aa1fe35880a1f1
Source dataset
uspto-grants-1990_09
Patent number
US04959359

Reaction notes

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