3-Chloro-4-methylaniline → HCID 68422227, compound

HRID 506434Notes

Reaction equation

HRID 506434 reaction equation
[CH:1]1([C:4]2(C(O)=O)[CH2:8][S:7][N:6]=[N:5]2)[CH2:3][CH2:2]1.[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C.[Cl:28][C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][C:35]=1[CH3:36])[NH2:32].C1C[O:40][CH2:39]C1>O>[Cl:28][C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][C:35]=1[CH3:36])[NH:32][C:39]([C:8]1[S:7][N:6]=[N:5][C:4]=1[CH:1]1[CH2:2][CH2:3]1)=[O:40]

Participants

7

Reactant 5

HCID 72553-Chloro-4-methylanilineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 68422664HCID 68422664, compound

Product 1

HCID 68422227HCID 68422227, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Cyclopropyl-1,2,3-thiadiazolecarboxylic acid (4 g; 24 mmols), 2-chloro-1-methylpyridinium iodide (7.2 g; 28 mmols), triethylamine (5.9 g; 58 mmols) and 3-chloro-4-methylaniline (3.7 g; 26 mmols) were dissolved or suspended in THF (50 ml), followed by stirring at room temperature for 10 hours. Water was added thereto to stop the reaction, the mixture was extracted with ethyl acetate. After drying over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to thereby obtain 6.9 g of 3′-chloro-4-cyclopropyl-4′-methyl-1,2,3-thiadiazole-5-carboxanilide.

Workup

  1. customthe reaction
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-c6ad853e5946439b8c7691bfb642029a
Source dataset
uspto-grants-2010_08
Patent number
US07786040B2

Reaction notes

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