Pyridine → HCID 18332426, compound

HRID 2268773Notes

Reaction equation

HRID 2268773 reaction equation
[CH3:1][S:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.[CH:15]([NH2:18])([CH3:17])[CH3:16].N1C=CC=CC=1.[Si](Cl)(Cl)(Cl)Cl>O>[CH3:16][CH:15]([NH:18][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([S:2][CH3:1])=[CH:4][C:5]=1[N+:12]([O-:14])=[O:13])[CH3:17]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6363IsopropylamineHCID 24816Silicon tetrachlorideHCID 13988043HCID 13988043, compound

Product 1

HCID 18332426HCID 18332426, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-methylthio-2-nitrobenzoic acid (3.07 g, 0.01439 mol) [Lit. Ref. DE 2421541], isopropylamine (1.47 ml, 0.01728 mol) and pyridine (100 ml) was cooled in an ice bath. Silicon tetrachloride (2.01 ml, 0.01728 mol) was added dropwise under nitrogen over 15 mins. After stirring at room temperature for 2 hr the solution was refluxed for 7 hr, then allowed to cool to room temperature. The solution was added to water and concentrated in vacuo. The precipitate was dissolved in dichloromethane and washed twice with 1N hydrochloric acid (150 ml), dried and concentrated in vacuo to afford 2.82 g of amorphous yellow solid. δ(1H NMR, CDCl3, ppm): 1.10 (6H, d), 2.50 (3H, s), 4.2 (1H, m), 5.50 (1H, s), 7.35 (2H, m), 7.75 (1H, s).

Workup

  1. temperaturewas refluxed for 7 hr
  2. temperatureto cool to room temperature
  3. concentrationconcentrated in vacuo
  4. dissolutionThe precipitate was dissolved in dichloromethane
  5. washwashed twice with 1N hydrochloric acid (150 ml)
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d46abf2bb31f4f308d12dc06535c8835
Source dataset
uspto-grants-2001_12
Patent number
US06329366B1

Reaction notes

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