Thiomorpholine → 4-[[(4-Thiomorpholinyl)methylene]amino]-3-pyridinol

HRID 361330

Reaction equation

HRID 361330 reaction equation
[CH3:1][N:2]([CH:4]=[N:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[OH:12])[CH3:3].N1C[CH2:17][S:16][CH2:15]C1>C1(C)C=CC=CC=1>[N:2]1([CH:4]=[N:5][C:6]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[OH:12])[CH2:1][CH2:17][S:16][CH2:15][CH2:3]1

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 153809294-[[(Dimethylamino)methylene]amino]-3-pyridinol

Product 1

HCID 153809384-[[(4-Thiomorpholinyl)methylene]amino]-3-pyridinol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture prepared from 4-[[(dimethylamino)methylene]amino]-3-pyridinol (5.14 g), thiomorpholine (10.5 ml, distilled from CaH2) and dry toluene (120 ml) was refluxed overnight. The reaction mixture was concentrated, triturated with diethyl ether, adhered to silica (methanol), flash chromatographed (10% methanol/ethyl acetate), and triturated with diethyl ether to yield 6.06 g of product. A 3.5 g sample was recrystallized from methanol, and dried under high vacuum and refluxing isopropanol to yield 2.13 g of crystals, m.p. 197°-198.5° C.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture was concentrated
  3. customtriturated with diethyl ether
  4. customchromatographed (10% methanol/ethyl acetate)
  5. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-2bc39261f74746edae224d78ee97c69e
Source dataset
uspto-grants-1999_02
Patent number
US05866565

Linked notes

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