Water → HCID 21852348, compound

HRID 617443Notes

Reaction equation

HRID 617443 reaction equation
Br[CH2:2][C:3]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])=[N:6][S:5][N:4]=1.[C-:15]#[N:16].[Na+].O>CN(C)C=O>[Cl:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]1[C:3]([CH2:2][C:15]#[N:16])=[N:4][S:5][N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 21852366HCID 21852366, compound

Product 1

HCID 21852348HCID 21852348, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide, 290 mg of 3-bromomethyl-4-(2-chlorophenyl)-1,2,5-thiadiazole, and 49 mg of sodium cyanide were stirred at 90° C. for 3 hours. After spontaneous cooling, the reaction mixture was poured into water, and was extracted with diethyl ether. The diethyl ether layer was washed with dilute sodium hydroxide solution and water, dried over anhydrous magnesium sulfate, and concentrated. The concentrate was purified by silica gel column chromatography to obtain 150 mg of 3-(2-chlorophenyl)-4-cyanomethyl-1,2,5-thiadiazole. The obtained 150 mg of 3-(2-chlorophenyl)-4-cyanomethyl-1,2,5-thiadiazole, 6 mL of 5% sodium hydroxide solution, and 2 mL of ethanol were mixed and refluxed by heating for one hour. After spontaneous cooling, the reaction mixture was poured into dilute hydrochloric acid, and was extracted with diethyl ether. The diethyl ether layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. The concentrate was purified by silica gel column chromatography to obtain 120 mg of [3-(2-chlorophenyl)-1,2,5-thiadiazole-4-yl]acetic acid.

Workup

  1. extractionwas extracted with diethyl ether
  2. washThe diethyl ether layer was washed with dilute sodium hydroxide solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-80b6f76c08da4b94b558f677086aae0f
Source dataset
uspto-grants-1999_09
Patent number
US05948916

Reaction notes

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