3,5-Dichloroaniline → HCID 9954089, compound

HRID 1531222Notes

Reaction equation

HRID 1531222 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].[C:10]([N:17]1[CH:21]=NC=N1)(N1C=NC=N1)=[S:11].NC1[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:3]=[C:4]([NH:5][C:10](=[S:11])[NH:17][C:21]2[CH:28]=[CH:27][C:26]([NH:29][C:30]([C:32]3[N:33]=[N:34][S:35][CH:36]=3)=[O:31])=[CH:25][CH:24]=2)[CH:6]=[C:7]([Cl:9])[CH:8]=1

Participants

5

Reactant 3

HCID 122813,5-DichloroanilineHCID 11137714Bis(1H-1,2,4-triazol-1-yl)methanethioneHCID 12051700HCID 12051700, compound

Product 1

HCID 9954089HCID 9954089, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,5-dichloroaniline (0.16 g) in tetrahydrofuran (20 ml) is added freshly prepared 1,1′-thiocarbonyl-di-(1,2,4)-triazole (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. [M+H] 424.

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-60d14f0ff2d94484866112a92f84f011
Source dataset
uspto-grants-2001_03
Patent number
US06197803B1

Reaction notes

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