Hydrochloric Acid → 1,2,4-Thiadiazole-3-carboxylic acid, 5-chloro-, methyl ester

HRID 543839Notes

Reaction equation

HRID 543839 reaction equation
N[C:2]1[S:6][N:5]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[N:3]=1.[ClH:11].N([O-])=O.[Na+]>O.[Cu]>[Cl:11][C:2]1[S:6][N:5]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 13577102Methyl 5-amino-1,2,4-thiadiazole-3-carboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 233241991,2,4-Thiadiazole-3-carboxylic acid, 5-chloro-, methyl ester

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of methyl 5-amino-1,2,4-thiadiazole-3-carboxylate (26 g), conc.hydrochloric acid (490 ml) and a small amount of copper was added dropwise over 40 minutes a solution of sodium nitrite (22.5 g) in water (28 ml) at -10° to -15° C. The mixture was stirred for 1.5 hours at the same temperature and for 30 minutes at 50° C. The reaction mixture was poured into ice-water (500 ml) and extracted with ethyl acetate. The extract was washed, dried and concentrated to give white powder of methyl 5-chloro-1,2,4-thiadiazole-3-carboxylate (8.9 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-620850f1f324403f981c8e85a9a62923
Source dataset
uspto-grants-1984_05
Patent number
US04447429

Reaction notes

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