Isopropanol → HCID 23371627, compound

HRID 1899809Notes

Reaction equation

HRID 1899809 reaction equation
[OH:1][CH:2]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH2:3][N:4]1[CH2:9][CH2:8][C:7]([C:10]2[S:11][CH2:12][C:13](=[O:16])[NH:14][N:15]=2)=[CH:6][CH2:5]1.[CH:25](O)([CH3:27])[CH3:26].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1C=CC=CC=1>[CH:25]([O:1][CH:2]([C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)[CH2:3][N:4]1[CH2:9][CH2:8][C:7]([C:10]2[S:11][CH2:12][C:13](=[O:16])[NH:14][N:15]=2)=[CH:6][CH2:5]1)([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 15290063HCID 15290063, compound

Product 1

HCID 23371627HCID 23371627, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-[1-[2-Hydroxy-2-(4-methoxyphenyl)ethyl]-1,2,5,6-tetrahydropyrid-4-yl]-4H,6H-1,3,4-thiadiazin-5-one (300 mg, 0.86 mmol) was suspended in mixed solution of isopropanol(15 ml) and benzene (25 ml), added with p-toluenesulfonic acid monohydrate (4.5 g, 0.02 mol) and refluxed for 5 hours while being dehydrated by a Dean-Stark's dehydrator. After allowing to cool to room temperature, the reaction mixture was added dropwise to 1N aqueous sodium hydroxide (30 ml). The benzen layer was separated and the water layer was further extracted three times with benzen. The benzen layer was combined with the above-mentioned benzen layer and dried over anhydrous magnesium sulfate. Benzene was removed under reduced pressure and the residue was crystallized from a little amount of ether. The solid obtained was further crystallized from ether to obtain the titled compound (145 mg) as white power.

Workup

  1. temperaturerefluxed for 5 hours
  2. customThe benzen layer was separated
  3. extractionthe water layer was further extracted three times with benzen
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customBenzene was removed under reduced pressure
  6. customthe residue was crystallized from a little amount of ether
  7. customThe solid obtained
  8. customwas further crystallized from ether

Sources & evidence

ORD record
ord-2281ec5a352c4ae4b4272d9de94ccf12
Source dataset
uspto-grants-1996_11
Patent number
US05574033

Reaction notes

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