Water → HCID 15023183, compound

HRID 1078185Notes

Reaction equation

HRID 1078185 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:24])[CH3:23].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:24])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 15023182HCID 15023182, compound

Product 1

HCID 15023183HCID 15023183, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution containing 0.49 g of 3-amino-4-(2,6-dichlorophenyl)-1,2,5-thiadiazole and 0.22 g of triethylamine in N,N-dimethylformamide, 0.20 g of acetyl chloride was added and the mixture was stirred 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 chromatography to obtain 0.25 g of 3-acetylamino-4-(2,6-dichlorophenyl)-1,2,5-thiadiazole.

Workup

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

Sources & evidence

ORD record
ord-8f13529acfda4ba485d78550bd9d7988
Source dataset
uspto-grants-1996_08
Patent number
US05547920

Reaction notes

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