Chloroacetic Acid → [(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetic acid

HRID 323523Notes

Reaction equation

HRID 323523 reaction equation
[OH-].[Na+].[SH:3][C:4]1[S:5][C:6]([CH3:9])=[N:7][N:8]=1.Cl[CH2:11][C:12]([OH:14])=[O:13].Cl>O.CO.C(O)C>[C:12]([CH2:11][S:3][C:4]1[S:5][C:6]([CH3:9])=[N:7][N:8]=1)([OH:14])=[O:13]

Participants

8

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 178434161HCID 178434161, compound

Product 1

HCID 589580[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetic acidYield 75%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent3×

Procedure

Aqueous solution of sodium hydroxide 8.8 g (0.22 mol) in 15 ml of water was added to a mixture of 2-mercapto-5-methyl-1,3,4-thiadiazole 26.4 g (0.20 mol), chloroacetic acid 27.0 g (0.22 mol) and ethanol 300 ml with stirring at room temperature. After 20 minutes of stirring it was heated to 50° C., and further aqueous solution of sodium hydroxide 8.8 g (0.22 mol) in 15 ml of water was added slowly drop by drop. After stirring for 3 hours at 50° C., it was cooled to room temperature, and water was added till reaction liquid became uniform. Hydrochloric acid was added for neutralization. Prepared crystal was collected by filtration and 28.7 g (0.150 mol) of 2-carboxymethylthio-5-methyl-1,3,4-thiadiazole was obtained by recrystallization in methanol. Yield 75%.

Workup

  1. stirringAfter 20 minutes of stirring it
  2. temperaturewas heated to 50° C.
  3. stirringAfter stirring for 3 hours at 50° C.
  4. temperatureit was cooled to room temperature
  5. customPrepared crystal
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-3904dc23cf5543ca916a97de073c3d95
Source dataset
uspto-grants-2001_04
Patent number
US06214533B1

Reaction notes

Loading…