2,5-Dichloroaniline → HCID 9888577, compound

HRID 1533237Notes

Reaction equation

HRID 1533237 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[NH2:4].[C:10](N1C=CN=C1)(N1C=CN=C1)=[S:11].[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([C:32]2[N:33]=[N:34][S:35][CH:36]=2)=[O:31])=[CH:25][CH:24]=1>O1CCCC1>[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[NH:4][C:10](=[S:11])[NH:22][C:23]1[CH:24]=[CH:25][C:26]([NH:29][C:30]([C:32]2[N:33]=[N:34][S:35][CH:36]=2)=[O:31])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 72622,5-DichloroanilineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 12051700HCID 12051700, compound

Product 1

HCID 9888577HCID 9888577, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,5-dichloroaniline (0.16 g) in tetrahydrofuran (20 mL) is added freshly prepared 1,1′-thiocarbonyldiimidazole (0.20 g) and the mixture is stirred for approximately 30 minutes at room temperature. [1,2,3]-Thiadiazole-4-carboxylic acid (4-amino-phenyl) amide (0.22 g) is added to the reaction flask and the mixture is stirred for approximately 6 hours. The solvent is then removed by evaporation under reduced pressure and warm acetonitrile (3 mL) is added. After 15 hours the mixture is filtered and the collected precipitate is washed with acetonitrile then diethyl ether, an air dried to provide the desired product as a white powder.

Workup

  1. stirringthe mixture is stirred for approximately 6 hours
  2. customThe solvent is then removed by evaporation under reduced pressure
  3. temperaturewarm acetonitrile (3 mL)
  4. additionis added
  5. filtrationAfter 15 hours the mixture is filtered
  6. washthe collected precipitate is washed with acetonitrile
  7. dry with materialdiethyl ether, an air dried

Sources & evidence

ORD record
ord-fab0db5c26e74db981f221e877bc67a8
Source dataset
uspto-grants-2001_03
Patent number
US06207715B1

Reaction notes

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