Thionyl Chloride → HCID 15168934, compound

HRID 1078553Notes

Reaction equation

HRID 1078553 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[NH2:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:26])=[CH:23][C:24]=1[OH:25].C(N(CC)C(C)C)(C)C>O.O1CCCC1>[Cl:1][C:2]1[C:3]([C:4]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([CH3:26])=[CH:23][C:24]=2[OH:25])=[O:6])=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][N:10]=1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 760822-Amino-5-methylphenolHCID 81531DiisopropylethylamineHCID 125426642-Chloro-5-nitropyridine-3-carboxylic acid

Product 1

HCID 15168934HCID 15168934, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-chloro-5-nitronicotinic acid (6.1 g, 0.03 mol) and thionyl chloride (15 ml) was refluxed for 3 hours. The solvent was removed in vacuo and the acid chloride was dissolved in tetrahydrofuran (150 ml). The resulting solution was slowly added to a solution of 6-amino-m-cresol (4 g, 0.03 mol), N,N-diisopropylethylamine (7 ml, 0.04 mol), and tetrahydrofuran (150 ml) at 0° C. under argon, and the resulting solution stirred for 2 hours. The mixture was then diluted with water and the product was extracted with ether, washed with a saturated sodium chloride solution, dried (anhydrous magnesium sulfate), and concentrated to half volume. The gummy orange crude product was collected and stirred with methylene chloride (50 ml) for 30 min. The precipitate was washed with methylene chloride and air dried to give 6.3 g (68% of theory) of pure product as a bright orange powder.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe acid chloride was dissolved in tetrahydrofuran (150 ml)
  4. extractionthe product was extracted with ether
  5. washwashed with a saturated sodium chloride solution
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. concentrationconcentrated to half volume
  8. customThe gummy orange crude product was collected
  9. stirringstirred with methylene chloride (50 ml) for 30 min
  10. washThe precipitate was washed with methylene chloride and air
  11. customdried
  12. customto give 6.3 g (68% of theory) of pure product as a bright orange powder

Sources & evidence

ORD record
ord-260ed2427cac4bc289a30797e2faeb6f
Source dataset
uspto-grants-1996_08
Patent number
US05550122

Reaction notes

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