Triethylamine → HCID 23107819, compound

HRID 1094972Notes

Reaction equation

HRID 1094972 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13](=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20]Cl)[CH:15]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C.[SH:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1.COC1C=C(C=CC=1OC)C(Cl)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13](=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][S:30][C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)[CH:15]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 77070Veratroyl chlorideHCID 23107570HCID 23107570, compoundHCID 178418431pyridine-4-thiol

Product 1

HCID 23107819HCID 23107819, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Subsequently, methyl 5-bromo-2-[3-(chloromethyl)benzoyl]aminobenzoate (1.5 g) was dissolved in anhydrous methylene chloride. Triethylamine (2.0 ml) and 4-mercaptopyridine (compound B′) (880 mg) were added to the solution at room temperature, and the mixture was stirred at that temperature for 12 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, was dried over sodium sulfate, and was then concentrated. Diethyl ether was added to the residue for crystallization. The crystals were filtered through Kiriyama Rohto (21 mmφ) and were washed with diethyl ether to give methyl 5-bromo-2-(3-[(4-pyridylsulfanyl)methyl]benzoylamino)benzoate (1.20 g, yield 67%) as a useful intermediate.

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionat room temperature, and the mixture was subjected to separatory extraction with chloroform
  5. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated
  8. additionDiethyl ether was added to the residue for crystallization
  9. filtrationThe crystals were filtered through Kiriyama Rohto (21 mmφ)
  10. washwere washed with diethyl ether

Sources & evidence

ORD record
ord-ab7c07bdbe4a4424991d77c59f404486
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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