Triethylamine → HCID 11485882, compound

HRID 1006394Notes

Reaction equation

HRID 1006394 reaction equation
[Cl:1][C:2]1[C:10]([N:11]2[C:15](=[O:16])[N:14]([CH3:17])[N:13]=[N:12]2)=[C:9]([Cl:18])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[C:19]1(=[O:26])[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[CH2:20]1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[C:10]([N:11]2[C:15](=[O:16])[N:14]([CH3:17])[N:13]=[N:12]2)=[C:9]([Cl:18])[CH:8]=[CH:7][C:3]=1[C:4]([CH:20]1[C:21](=[O:25])[CH2:22][CH2:23][CH2:24][C:19]1=[O:26])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104341,3-CyclohexanedioneHCID 11150959HCID 11150959, compound

Product 1

HCID 11485882HCID 11485882, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dichloromethane solution of the crude 2,4-dichloro-3-(4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl)benzoyl chloride (1.10 g) was added drop by drop to the solution of 1,3-cyclohexanedione (0.44 g) and triethylamine (0.43 g) in dichloro-methane (8 ml) at 5° C. and the mixture was stirred at room temperature for 6 hours. After completion of the reaction it was extracted with dichloromethane (150 ml), washed with diluted hydrochloric acid and aqueous solution of sodium hydrogen carbonate and then dried with anhydrous magnesium sulfate. The residue, obtained by distilling off the dichloromethane, was dissolved in acetonitrile (7 ml), added with triethylamine (0.43 g) and acetonecyanohydrin (18 mg) and stirred at room temperature for 8 hours. After the solvent was distilled off, the residue was acidified by addition of diluted hydrochloric acid and extracted with ethyl acetate (150 ml). The organic layer was washed with saturated salt water and dried with anhydrous magnesium sulfate. By distilling off the ethyl acetate, the objective 2-[2,4-dichloro-3-(4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl )benzoyl]cyclohexan-1,3-dione (0.70g, 51% yield from 2,4-dichloro-3-(4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl)benzoic acid) was obtained. mp 138-140° C.

Workup

  1. customAfter completion of the reaction it
  2. extractionwas extracted with dichloromethane (150 ml)
  3. washwashed with diluted hydrochloric acid and aqueous solution of sodium hydrogen carbonate
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe residue, obtained
  6. distillationby distilling off the dichloromethane
  7. dissolutionwas dissolved in acetonitrile (7 ml)
  8. additionadded with triethylamine (0.43 g) and acetonecyanohydrin (18 mg)
  9. stirringstirred at room temperature for 8 hours
  10. distillationAfter the solvent was distilled off
  11. additionthe residue was acidified by addition of diluted hydrochloric acid
  12. extractionextracted with ethyl acetate (150 ml)
  13. washThe organic layer was washed with saturated salt water
  14. dry with materialdried with anhydrous magnesium sulfate
  15. distillationBy distilling off the ethyl acetate

Sources & evidence

ORD record
ord-f28e679edbb740d9a9049a32d4ce407a
Source dataset
uspto-grants-2004_09
Patent number
US06790810B2

Reaction notes

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