Pyridine → HCID 57842864, compound

HRID 735524Notes

Reaction equation

HRID 735524 reaction equation
C(Cl)(=O)C(Cl)=O.[CH:7]([S:10][C:11]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:12]=1[C:13](O)=[O:14])([CH3:9])[CH3:8].Cl.CN.[N:26]1C=CC=C[CH:27]=1>C(Cl)Cl.CN(C=O)C>[CH:7]([S:10][C:11]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:12]=1[C:13]([NH:26][CH3:27])=[O:14])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 6364545Methylamine hydrochlorideHCID 578427985-Nitro-2-(propan-2-ylsulfanyl)benzoic acid

Product 1

HCID 57842864HCID 57842864, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (1.75 mL, 19.6 mmol) was added dropwise to a suspension of 16A (2.41 g, 10 mmol) in DCM (20 mL) containing DMF (2 drops) at 0° C. The reaction mixture was warmed to rt and stirred overnight. The reaction mixture was concentrated in vacuo and coevaporated twice with toluene. The residue was dissolved in DCM (25 mL) and added portionwise to a solution of methylamine hydrochloride (2.03 g, 30.1 mmol) and pyridine (8.1 mL, 100 mmol) in DCM (25 mL) at 0° C. The reaction mixture was stirred overnight at rt. The reaction mixture was concentrated in vacuo and the residue was triturated with water to give 16B (2.08 g, 82%) as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in DCM (25 mL)
  3. stirringThe reaction mixture was stirred overnight at rt
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe residue was triturated with water

Sources & evidence

ORD record
ord-7f4b17e3697c4402a024b53b09fbb03a
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

Loading…