3,5-Dichloroaniline → HCID 9954089, compound

HRID 1385277Notes

Reaction equation

HRID 1385277 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-c12dcc088fc246929ebc44349e2d288b
Source dataset
uspto-grants-2001_07
Patent number
US06262090B1

Reaction notes

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