Water → HCID 86625501, compound

HRID 2263144Notes

Reaction equation

HRID 2263144 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([NH2:7])[S:4][N:3]=1.N1C=CC=CC=1.Cl[C:15]([O:17][CH2:18][C:19]([Cl:22])([Cl:21])[Cl:20])=[O:16].O>O1CCCC1>[CH3:1][C:2]1[N:6]=[C:5]([NH:7][C:15](=[O:16])[O:17][CH2:18][C:19]([Cl:22])([Cl:21])[Cl:20])[S:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 3506395-Amino-3-methyl-1,2,4-thiadiazole

Product 1

HCID 86625501HCID 86625501, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-methyl-1,2,4-thiadiazol-5-amine (1.00 g, 8.68 mmol) and pyridine (0.850 ml, 10.4 mmol) in tetrahydrofuran (30 ml) was added 2,2,2-trichloroethyl chloroformate (1.44 ml, 10.4 mmol) with ice-cooling and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. Hexane was poured to the residue and a solid was collected by filtration to obtain the desired product (1.84 g, 72.8%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionHexane was poured to the residue
  7. filtrationa solid was collected by filtration

Sources & evidence

ORD record
ord-e0215f1253b04c5d93815bbdae815369
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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