2,5-Dichloroaniline → HCID 9888577, compound

HRID 990884Notes

Reaction equation

HRID 990884 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, and 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, and air dried

Sources & evidence

ORD record
ord-d362a99ba5444af8b33282308aeff5df
Source dataset
uspto-grants-2002_10
Patent number
US06462055B2

Reaction notes

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