Hydrochloric Acid → HCID 21184064, compound

HRID 866757Notes

Reaction equation

HRID 866757 reaction equation
[S-:1][C:2]#[N:3].[Na+].Cl[C:6]([O:8][CH2:9][CH3:10])=[O:7].[N+:11](=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N-:12].Cl>C(#N)C>[CH2:9]([O:8][C:6]([NH:3][C:2]1[S:1][N:12]=[N:11][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:7])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 12192Ethyl diazoacetateHCID 516871Sodium thiocyanate

Product 1

HCID 21184064HCID 21184064, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
19 °C

Procedure

A suspension of sodium thiocyanate (24.30 g, 0.30 mole) in acetonitrile (120 ml), maintained at 19° C., was treated dropwise over 22 minutes with a solution of ethyl chloroformate (28.7 ml, 0.30 mole) in acetonitrile (25 ml). The resultant mixture was stirred for 25 minutes at 20° C. and then ethyl diazoacetate (31.5 ml, 0.30 mole) was added. After stirring for 24 hours, 6.0 N hydrochloric acid (300 ml) was added with cooling. Acetonitrile solvent was removed in vacuo and the residual aqueous suspension was extracted several times with ether. Combined ether extracts were washed with water, dried (Na2SO4) and evaporated to leave 51.0 g of ethyl 5-ethoxycarbonylamino-1,2,3-thiadiazole-4-carboxylate. This ester was hydrolyzed by refluxing for 6 hours in a mixture of ethanol (80 ml) and aqueous 6 N hydrochloric acid (400 ml) to yield the title acid; m.p. 179°-180° dec. after crystallization from nitromethane.

Workup

  1. temperaturewith cooling
  2. customAcetonitrile solvent was removed in vacuo
  3. extractionthe residual aqueous suspension was extracted several times with ether
  4. washCombined ether extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-c8cb29d989d94c32b8a69030a3440798
Source dataset
uspto-grants-1978_07
Patent number
US04101548

Reaction notes

Loading…