Dichloromethane → 4-methyl-N-(4-methylphenyl)-N-morpholinothio-1,2,3-thiadiazole-5-carboxamide

HRID 1699653

Reaction equation

HRID 1699653 reaction equation
C(Cl)Cl.[CH3:4][C:5]1[N:6]=[N:7][S:8][C:9]=1[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=[O:11].Cl[S:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(N(CC)CC)C>O>[CH3:4][C:5]1[N:6]=[N:7][S:8][C:9]=1[C:10]([N:12]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)[S:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[O:11]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 8508264-methyl-N-(4-methylphenyl)-1,2,3-thiadiazole-5-carboxamideHCID 122977794-Morpholinesulfenyl chloride

Product 1

HCID 159066254-methyl-N-(4-methylphenyl)-N-morpholinothio-1,2,3-thiadiazole-5-carboxamideYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 10 ml of methylene chloride were added 0.50 g (2.1 mmol) of 4-methyl-N-(4-methylphenyl)-1,2,3-thiadiazole-5-carboxamide and 0.50 g (3.3 mmol) of N-(chlorosulfenyl)morpholine. Then, 0.33 g (3.3 mmol) of triethylamine was slowly added thereto, and the resulting mixture was reacted with stirring for 5 hours. After the reaction was completed, the reaction mixture containing the objective product was poured into water, the objective product was extracted with ethyl acetate, the organic layer was washed with water and dried on anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the crude crystal thus obtained was washed with ether. As a result, 0.38 g of the objective compound was obtained (Property: m.p. 60° C. (decomposed); Yield: 52%).

Workup

  1. customthe resulting mixture was reacted
  2. additionthe reaction mixture containing the objective product
  3. extractionthe objective product was extracted with ethyl acetate
  4. washthe organic layer was washed with water
  5. dry with materialdried on anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe crude crystal thus obtained
  8. washwas washed with ether

Sources & evidence

ORD record
ord-9cc0f3aa999e4288ac25e7d0812b3bd0
Source dataset
uspto-grants-2002_02
Patent number
US06348460B1

Linked notes

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