Hydrochloric Acid → 2-Chloro-5-phenyl-1,3,4-thiadiazole

HRID 1593952Notes

Reaction equation

HRID 1593952 reaction equation
S(O)(O)(=O)=O.N[C:7]1[S:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][N:11]=1.N([O-])=O.[Na+].[ClH:22]>>[Cl:22][C:7]1[S:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][N:11]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 162130872-amino-5-phenyl-1,3,4-thiadiazole sulfate saltHCID 23668193Sodium Nitrite

Product 1

HCID 2531452-Chloro-5-phenyl-1,3,4-thiadiazole

Conditions

Temperature
0 °C

Procedure

A mixture of 2-amino-5-phenyl-1,3,4-thiadiazole sulphate (10.0 g, 56.4 mmol) and conc. hydrochloric acid (100 ml) was stirred at 0° C. Sodium nitrite (5.06 g, 69 mmol) was added at 0° C. The mixture was stirred for 9 days at room temperature. The crystals were filtered and resuspended in aqueous hydrochloric acid (150 ml, 1M), stirred overnight and filtered. Aqueous sodium hydroxide (100 ml, 4 M) was added and extracted with ethyl acetate. Yield 5.68 g.

Workup

  1. stirringThe mixture was stirred for 9 days at room temperature
  2. filtrationThe crystals were filtered
  3. stirringstirred overnight
  4. filtrationfiltered
  5. additionAqueous sodium hydroxide (100 ml, 4 M) was added
  6. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-39878e2b5ab24c0081acebff09b8dad6
Source dataset
uspto-grants-2007_11
Patent number
US07300933B2

Reaction notes

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