Toluene → HCID 67854448, compound

HRID 1646952Notes

Reaction equation

HRID 1646952 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][NH:14]2)=[O:9].C1(C)C=CC=CC=1.S(O[CH2:37][CH2:38][Cl:39])(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.C(#N)C>[Cl:39][CH2:38][CH2:37][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][NH:14]2)=[O:9]

Participants

8

Reactant 4

HCID 1140TolueneHCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 14798Sodium HydroxideHCID 14880469HCID 14880469, compound

Product 1

HCID 67854448HCID 67854448, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

6 g of the product of Step D of Example 3, 192 ml of toluene, 90 ml of acetonitrile, 2.16 g of tetrabutyl ammonium hydrogen sulfate, 9.18 ml of 2-chloroethanol tosylate and 90 ml of 5N sodium hydroxide were stirred for 72 hours at 50° C. The mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed, dried and concentrated to dryness under reduced pressure. The residue was chromatographed on silica (eluant: methylene chloride) to obtain 5.39 g of the desired product which was used as is for the following step.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed
  3. customdried
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue was chromatographed on silica (eluant: methylene chloride)

Sources & evidence

ORD record
ord-5471499c8b184f038c2c135b4b3e4a61
Source dataset
uspto-grants-1993_01
Patent number
US05182282

Reaction notes

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