p-Toluenesulfonic acid → HCID 19898835, compound

HRID 1196529Notes

Reaction equation

HRID 1196529 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]([N:13]2[CH:18]([CH2:19][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:17][CH2:16][C:15](=[O:25])[CH2:14]2)=[O:12])[CH:6]=[CH:7][C:8]=1[Cl:9].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:37](O)([OH:39])[CH3:38]>C1(C)C=CC=CC=1.ClCCl>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]([N:13]2[CH:18]([CH2:19][N:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)[CH2:17][CH2:16][C:15]3([O:39][CH2:37][CH2:38][O:25]3)[CH2:14]2)=[O:12])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 1512111,1-EthanediolHCID 19898872HCID 19898872, compound

Product 1

HCID 19898835HCID 19898835, compoundYield 135.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of the product of Example 25 (0.16 g) p-toluenesulphonic acid (0.14 g) and ethanediol (0.1 g) in dry toluene (10 ml) was heated under Dean and Starke conditions for 2 hours. The cooled reaction mixture was diluted with dichloromethane (50 ml) and the organic solution was washed with aqueous sodium carbonate solution (1M; 2×15 ml). The organic solution was dried and evaporated in vacuo. The residue was purified by flash chromatography eluting with dichloromethane/methanol/ammonia (200:8:1) to give the free base of the title compound as a gum (0.12 g). A solution of the free base in dry diethyl ether (10 ml) was treated with ethereal hydrogen chloride. The resulting precipitate was washed with diethyl ether (10 ml) to give the title compound as a solid (0.10 g) m.p. 255° dec. T.l.c. SiO2 (dichloromethane/methanol/ammonia 150:8:1) Rf 0.3.

Workup

  1. temperaturewas heated under Dean and Starke conditions for 2 hours
  2. customThe cooled reaction mixture
  3. washthe organic solution was washed with aqueous sodium carbonate solution (1M; 2×15 ml)
  4. customThe organic solution was dried
  5. customevaporated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluting with dichloromethane/methanol/ammonia (200:8:1)

Sources & evidence

ORD record
ord-65fe3c28366b47c0b10b217113eb44c5
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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