2-Chloro-5-nitrobenzoic acid → HCID 23291050, compound

HRID 365643Notes

Reaction equation

HRID 365643 reaction equation
[H-].[Na+].Cl[C:4]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][SH:25])=[CH:20][CH:19]=1>CN(C)C=O>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][S:25][C:4]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:5]=2[C:6]([OH:8])=[O:7])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 172872-Chloro-5-nitrobenzoic acidHCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiol

Product 1

HCID 23291050HCID 23291050, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% dispersion in mineral oil, 3.6 g, 0.088 mol) was added to a cold solution of 2-chloro-5-nitrobenzoic acid (16.1 g, 0.08 mol) in dimethylformamide (200 mL) and the mixture was stirred for 5 min. The cold mixture was treated dropwise with a solution of 4-methoxy-α-toluenethiol (13.2 g, 0.08 mol) in dimethylformamide (80 mL) and stirred at room temperature for 16 h. The mixture was concentrated in vacuo, and the residue was diluted with water and acidified with dilute hydrochloric acid to pH 1. The resulting precipitate was filtered, washed with water and azeotroped to dryness from a mixture of methylene chloride-toluene. The residue was suspended in ethyl ether, filtered and washed with ethyl ether to give the title compound as a yellow solid (16 g, 63%), which was used without further purification. Mp 200-204° C.

Workup

  1. stirringstirred at room temperature for 16 h
  2. concentrationThe mixture was concentrated in vacuo
  3. additionthe residue was diluted with water
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water
  6. customazeotroped to dryness from a mixture of methylene chloride-toluene
  7. filtrationfiltered
  8. washwashed with ethyl ether

Sources & evidence

ORD record
ord-d522df144ce646d8a418cc09ff70de7f
Source dataset
uspto-grants-2000_10
Patent number
US06127359

Reaction notes

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