Hydrochloric Acid → HCID 825760, compound

HRID 477872Notes

Reaction equation

HRID 477872 reaction equation
N([O-])=O.[Na+].[CH3:5][S:6][C:7]1[S:8][C:9]([C:13]#[N:14])=[C:10](N)[N:11]=1.Cl.C(Cl)[Cl:17]>O>[CH3:5][S:6][C:7]1[S:8][C:9]([C:13]#[N:14])=[C:10]([Cl:17])[N:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 6764114-Amino-2-(methylsulfanyl)-1,3-thiazole-5-carbonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 825760HCID 825760, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

A concentrated solution of 42 g of sodium nitrite in water is slowly added dropwise to a mixture of 68.4 g of 2-methylthio-4-amino-5-cyanothiazole, obtained according to example III, 100 ml of water, 300 ml of concentrated hydrochloric acid, 70 g of cuprous chloride (CuCl2.2H2O) and 800 ml of methylene chloride while stirring and cooling at approximately 0° C. After stirring for another 30 minutes at 0°-5° C. the mixture is diluted with water. The reaction mixture is filtered off and the filtrate is separated; the organic layer is washed with water, dried, filtered and evaporated while adding isopropanol until crystallisation. The desired compound is obtained in a yield of 46.3 g; m.p. 83°-87° C.

Workup

  1. customobtained
  2. stirringAfter stirring for another 30 minutes at 0°-5° C. the mixture
  3. filtrationThe reaction mixture is filtered off
  4. customthe filtrate is separated
  5. washthe organic layer is washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. additionwhile adding isopropanol
  10. customuntil crystallisation

Sources & evidence

ORD record
ord-f0594a10bb744a498f19cca39c976726
Source dataset
uspto-grants-1989_12
Patent number
US04889863

Reaction notes

Loading…