Water → HCID 15023188, compound

HRID 1440654Notes

Reaction equation

HRID 1440654 reaction equation
[NH2:1][C:2]1[C:6]([C:7]2[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:14])=[N:5][S:4][N:3]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:26])[CH:23]([CH3:25])[CH3:24].O>CN(C)C=O>[C:22]([NH:1][C:2]1[C:6]([C:7]2[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:14])=[N:5][S:4][N:3]=1)(=[O:26])[CH:23]([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 15023182HCID 15023182, compound

Product 1

HCID 15023188HCID 15023188, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 0.49 g of 3-amino-4-(2,6-dichlorophenyl)-1,2,5-thiadiazole and 0.22 g of triethylamine in N,N-dimethylformamide, 0.27 g of isobutyryl chloride was added and the mixture was heated at 60° C. for 12 hours. After allowing to cool, the mixture was poured into water and was extracted with ether. The ether layer was washed twice with dilute hydrochloric acid, twice with water and twice with saturated aqueous sodium chloride solution. The resultant was dried over anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography to obtain 0.23 g of 3-isobutyrylamino-4-(2,6-dichlorophenyl)-1,2,5-thiadiazole.

Workup

  1. temperatureto cool
  2. extractionwas extracted with ether
  3. washThe ether layer was washed twice with dilute hydrochloric acid, twice with water and twice with saturated aqueous sodium chloride solution
  4. dry with materialThe resultant was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-c53a9f22e99f4d7a96e61ceff350742f
Source dataset
uspto-grants-1996_03
Patent number
US05500408

Reaction notes

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