Hydrochloric Acid → 19430-31-0

HRID 1262831Notes

Reaction equation

HRID 1262831 reaction equation
[ClH:1].N[C:3]1[S:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[N:6][N:7]=1.N([O-])=O.[Na+]>O>[Cl:1][C:3]1[S:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[N:6][N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6683925-(4-Chlorophenyl)-1,3,4-thiadiazol-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 1331877519430-31-0

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

Stirred 37% hydrochloric acid, 225 ml, was cooled in a salt-ice bath, and 2-amino-5-(4-chlorophenyl)-1,3,4-thiadiazole (18.3 g, 0.087 mole) was added. The mixture was cooled to -5° C., and a solution of sodium nitrite (25.0 g, 0.338 mole) in 100 ml of water was added dropwise during a one hour period. Upon complete addition, the reaction mixture was allowed to warm to room temperature, where it was stirred for 16 hours. The reaction mixture was heated for one hour on a steam bath, cooled, then filtered to isolate the precipitated solid. The solid was recrystallized from ethanol to give 2-chloro-5-(4-chlorophenyl)-1,3,4-thiadiazole (6.0 g, mp 125°-127° C.).

Workup

  1. temperaturewas cooled in a salt-ice bath
  2. additionUpon complete addition
  3. temperatureto warm to room temperature
  4. temperatureThe reaction mixture was heated for one hour on a steam bath
  5. temperaturecooled
  6. filtrationfiltered
  7. customto isolate the precipitated solid
  8. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-ee467a54324c421591f0c6b8cc8780de
Source dataset
uspto-grants-1984_06
Patent number
US04454147

Reaction notes

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