2,5-Dichloroaniline → HCID 9888577, compound

HRID 844331Notes

Reaction equation

HRID 844331 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 reduce 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
  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-3172a068aa2948849dcb103e1eaa5bda
Source dataset
uspto-grants-2002_04
Patent number
US06380243B1

Reaction notes

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